Compound for organic electric element, organic electric element comprising the same and electronic device thereof

ABSTRACT

Provided are a compound of Formula 1 and an organic electric element including a first electrode, a second electrode, and an organic material layer between the first and the second electrodes, where the organic material layer contains the compound of Formula 1 and improves luminous efficiency, stability, and life span of the element.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a Continuation-in-Part of U.S. patent applicationSer. No. 14/362,406 filed Jun. 3, 2014, which was a National PhaseApplication filed under 35 U.S.C. §371 as a national stage ofPCT/KR2012/011234, filed on Dec. 21, 2012, an application claiming thebenefit under 35 U.S.C. §119 of Korean Application No. 10-2012-0005545filed on Jan. 18, 2012 and Korean Application No. 10-2012-0118629, filedon Oct. 24, 2012, which is incorporated herein by reference in theirentirety.

BACKGROUND

Technical Field

The present invention relates to a compound for an organic electricelement, an organic electric element using the same, and an electronicdevice thereof.

Background Art

In general, an organic light emitting phenomenon refers to a phenomenonin which electric energy is converted into light energy by means of anorganic material. An organic electric element utilizing the organiclight emitting phenomenon usually has a structure including an anode, acathode, and an organic material layer interposed therebetween. Here, inmany cases, the organic material layer may have a multilayered structureincluding multiple layers made of different materials in order toimprove the efficiency and stability of an organic electric element, andfor example, may include a hole injection layer, a hole transport layer,a light emitting layer, an electron transport layer, an electroninjection layer, and the like.

A material used as an organic material layer in an organic electricelement may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material, and the like according to its function.

The most problematic issues in an organic electric element are life spanand efficiency, and the situation is such that this life span orefficiency issue must be solved as displays become larger and larger.Efficiency, life span, driving voltage, and the like are correlated witheach other. For example, if efficiency is increased, then drivingvoltage is relatively lowered, and the crystallization of an organicmaterial due to Joule heating generated during operation is reduced asdriving voltage is lowered, as a result of which life span shows atendency to increase.

However, efficiency cannot be maximized only by simply improving theorganic material layer. This is because long life span and highefficiency can be simultaneously achieved when an optimal combination ofenergy levels and T1 values, inherent material properties (mobility,interfacial properties, etc.), and the like among the respective layersincluded in the organic material layer is given.

Further, in order to solve the emission problem with a hole transportlayer in a recent organic electric element, an emission-auxiliary layeris present between the hole transport layer and a light emitting layer,and it is time to develop different emission-auxiliary layers accordingto respective light emitting layers (R, G, B). In general, an electrontransferred from an electron transport layer to a light emitting layerand a hole transferred from a hole transport layer to the light emittinglayer are recombined to form an exciton. However, since materials to beused in the hole transport layer must have low HOMO values, they mostlyhave low T1 values, and on account of this, the exciton formed in thelight emitting layer is transferred into the hole transport layer, whichcauses charge unbalance in the light emitting layer and thus lightemission at the light emitting layer-hole transport layer interface.

The light emission at the light emitting layer-hole transport layerinterface has a problem in that color purity and efficiency are loweredand life span is shortened. Therefore, there is an urgent need todevelop an emission-auxiliary layer which has a high T1 value and theHOMO level of which is between the HOMO energy level of a hole transportlayer and the HOMO energy level of a light emitting layer.

In addition, it is required to develop a hole injection layer materialthat retards penetration/diffusion of metal oxides from an anodeelectrode (ITO) into an organic layer, which is one cause for theshortened life span of an organic electric element, and has stabilityagainst Joule heat generated during the operation of an organic electricelement, that is, a high glass transition temperature. Also, it has beenreported that a low glass transition temperature of a hole transportlayer material has a great effect on the life span of an organicelectric element because the uniformity of a thin film surface collapsesduring the operation of the element. In general, deposition is a mainmethod of forming an OLED, and thus there is an actual need to develop amaterial that is durable to such a deposition method, that is, a highlyheat-resistant material.

In order to allow an organic electric element to fully exhibit theabove-mentioned excellent features, it should be prerequisite to supporta material constituting an organic material layer in the element, forexample, a hole injection material, a hole transport material, a lightemitting material, an electron transport material, an electron injectionmaterial, or the like, by a stable and efficient material. However, sucha stable and efficient organic material layer material for an organicelectric element has not yet been fully developed. Accordingly, there isa continuous need to develop new materials for an organic materiallayer.

SUMMARY

In order to solve the above-mentioned problems occurring in the priorart, an object of the present invention is to provide a compoundincluding a five-membered hetero ring, which allows an organic electricelement to have high luminous efficiency and low driving voltage and tobe improved in color purity and life span, an organic electric elementusing the same, and an electronic device including the organic electricelement.

In accordance with an aspect of the present invention, there is provideda compound represented by Formula below.

In another aspect of the present invention, there are provided anorganic electric element using the compound represented by Formula aboveand an electronic device including the organic electric element.

By using the compound according to embodiments of the present invention,an organic electric element not only has low driving voltage, but canalso be significantly improved in color purity, luminous efficiency, andlife span.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrates an example of an organic light emitting diodeaccording to an embodiment of the present invention.

FIG. 2 illustrates a graph for electron mobility of an EL deviceaccording to an embodiment of the present invention having the organicmaterial layers sequentially formed by an anode, an electron injectionlayer, an electron transport layer, a light emitting layer, an electrontransport layer, an electron injection layer and cathode.

FIG. 3 illustrates a graph for hole mobility of an EL device accordingto an embodiment of the present invention having the organic materiallayers sequentially formed by an anode, a hole injection layer, a holetransport layer, a light emitting layer, a hole transport layer, a holeinjection layer and cathode.

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail with reference to the accompanying illustrative drawings.

In designation of reference numerals to components in respectivedrawings, it should be noted that the same elements will be designatedby the same reference numerals although they are shown in differentdrawings. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif it is described in the specification that one component is“connected,” “coupled” or “joined” to another component, a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components, although the first component may be directlyconnected, coupled or joined to the second component.

Unless otherwise stated, the term “halo” or “halogen” as used hereinincludes fluorine, chlorine, bromine, and iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group” as usedherein has, but not limited to, 1 to 60 carbon atoms.

Unless otherwise stated, the term “alkenyl” or “alkynyl” as used hereinhas, but not limited to, double or triple bonds of 2 to 60 carbon atoms.

Unless otherwise stated, the term “cycloalkyl” as used herein means, butnot limited to, alkyl forming a ring having 3 to 60 carbon atoms.

Unless otherwise stated, the term “alkoxy group” as used herein has, butnot limited to, 1 to 60 carbon atoms.

Unless otherwise stated, the term “aryl group” or “arylene group” asused herein has, but not limited to, 6 to 60 carbon atoms.

Herein, the aryl group or arylene group means a monocyclic or polycyclicaromatic group, and examples of the aryl group may include a phenylgroup, a biphenyl group, a fluorine group, and a spiro fluorene group,but are not limited thereto.

Unless otherwise stated, the term “hetero alkyl” as used herein meansalkyl containing one or more hetero atoms.

Unless otherwise stated, the term “hetero aryl group” or “hetero arylenegroup” as used herein means, but not limited to, a C₃ to C₆₀ aryl orarylene group containing one or more hetero atoms, includes bothmonocyclic and poly cyclic rings, and may also be formed in conjunctionwith an adjacent group.

Unless otherwise stated, the term “heterocyclic alkyl” or “heterocyclicgroup” as used herein contains one or more hetero atoms, has 2 to 60carbon atoms, includes both monocyclic and polycyclic rings, and mayalso be formed in conjunction with an adjacent group. Also, theheterocyclic group may mean an alicyclic and/or aromatic groupcontaining hetero atoms.

Unless otherwise stated, the term “heteroatom” as used herein representsat least one of N, O, S, P, and Si.

Unless otherwise stated, the term “aliphatic” as used herein means analiphatic hydrocarbon having 1 to 60 carbon atoms, and the term“aliphatic ring” as used herein means an aliphatic hydrocarbon ringhaving 3 to 60 carbon atoms.

Unless otherwise stated, the term “saturated or unsaturated ring” meansa saturated or unsaturated aliphatic ring, an aromatic ring having 6 to60 carbon atoms, or a hetero ring.

Hetero compounds or hetero radicals other than the above-mentionedhetero compounds each contain, but not limited to, one or more heteroatoms.

Unless otherwise stated, the term “substituted or unsubstituted” as usedherein means that substitution is carried out by at least onesubstituent selected from the group consisting of, but not limited to,deuterium, halogen, an amino group, a nitrile group, a nitro group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkylamine group, aC₁-C₂₀ alkylthio group, a C₆-C₂₀ arylthio group, a C₂-C₂₀ alkenyl group,a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, a C₆-C₆₀ aryl group,a C₆-C₂₀ aryl group substituted by deuterium, a C₈-C₂₀ aryl alkenylgroup, a silane group, a boron group, a germanium group, and a C₅-C₂₀heterocyclic group.

FIG. 1 illustrates an organic electric element according to anembodiment of the present invention.

Referring to FIG. 1, an organic electric element 100 according to anembodiment of the present invention includes a first formed on asubstrate 100, a second electrode 180, and an organic material layerbetween the first electrode 120 and the second electrode 180, whichcontains the compound represented by Formula 1. Here, the firstelectrode 120 may be an anode (positive electrode), and the secondelectrode 180 may be a cathode (negative electrode). In the case of aninverted organic electric element, the first electrode may be a cathode,and the second electrode may be an anode.

The organic material layer includes a hole injection layer 130, a holetransport layer 140, a light emitting layer 150, an electron transportlayer 160, and an electron injection layer 170 formed in sequence on thefirst electrode 120. Here, the layers included in the organic materiallayer, except the light emitting layer 150, may not be formed. Theorganic material layer may further include a hole blocking layer, anelectron blocking layer, an emission-auxiliary layer 151, a buffer layer141, etc., and the electron transport layer 160 and the like may serveas the hole blocking layer.

Although not shown, the organic electric element according to anembodiment of the present invention may further include at least oneprotective layer formed on at least one of the sides the first andsecond electrodes, which is opposite to the organic material layer.

The inventive compound employed in the organic material layer may beused as a host material, a dopant material, or a capping layer materialin the hole injection layer 130, the hole transport layer 140, theelectron transport layer 160, the electron injection layer 170, or thelight emitting layer 150. For example, the inventive compound may beused as the light emitting layer 150, the hole transport layer 140,and/or the emission-auxiliary layer 151.

Since depending on the type and position of a substituent to beattached, a band gap, electrical properties, interfacial properties, andthe like may vary even in the same core, long life span and highefficiency can be simultaneously achieved when an optimal combination ofenergy levels and T1 values, inherent material properties (mobility,interfacial properties, etc.), and the like among the respective layersincluded in the organic material layer is given.

As already described above, in order to solve the emission problem witha hole transport layer in a conventional organic electric element, anemission-auxiliary layer is preferably formed between the hole transportlayer and a light emitting layer, and it is time to develop differentemission-auxiliary layers according to respective light emitting layers(R, G, B). However, even when a similar core is used, it is verydifficult to infer the characteristics of an emission-auxiliary layer ifa used organic material layer varies because the correlation between theemission-auxiliary layer and a hole transport layer and the correlationbetween the emission-auxiliary layer and a light emitting layer (host)mused be discovered.

Accordingly, in the present invention, a combination of energy levelsand T1 values, inherent material properties (mobility, interfacialproperties, etc.), and the like among the respective layers included inthe organic material layer is optimized by forming the light emittinglayer by using the compound represented by Formula 1, and thus the lifespan and efficiency of the organic electric element can be improved atthe same time.

The organic electric element according to an embodiment of the presentinvention may be manufactured using a PVD (physical vapor deposition)method. For example, the organic electric element may be manufactured bydepositing a metal, a conductive metal oxide, or a mixture thereof onthe substrate 110 to form the anode 120, forming the organic materiallayer including the hole injection layer 130, the hole transport layer140, the light emitting layer 150, the electron transport layer 160, andthe electron injection layer 170 thereon, and then depositing amaterial, which can be used as the cathode 180, thereon.

Also, the organic material layer may be manufactured in such a mannerthat a smaller number of layers are formed using various polymermaterials by a soluble process or solvent process, for example, spincoating, dip coating, doctor blading, screen printing, inkjet printing,or thermal transfer, instead of deposition. Since the organic materiallayer according to the present invention may be formed in various ways,the scope of protection of the present invention is not limited by amethod of forming the organic material layer.

According to used materials, the organic electric element according toan embodiment of the present invention may be of a top emission type, abottom emission type, or a dual emission type.

Further, the organic electric element according to an embodiment of thepresent invention may be any one of an organic light emitting diode(OLED), an organic solar cell, an organic photo conductor (OPC), anorganic transistor (organic TFT), and an element for monochromatic orwhite illumination.

Another embodiment of the present invention provides an electronicdevice including a display device, which includes the above describedorganic electric element, and a control unit for controlling the displaydevice. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a PDA, an electronicdictionary, a PMP, a remote controller, a navigation unit, a gameplayer, various kinds of TVs, and various kinds of computers.

Hereinafter, a compound according to an aspect of the present inventionwill be described.

The compound according to an aspect of the present invention isrepresented by Formula 1 below.

In Formula 1 above, R₁ to R₄ and R₁₁ to R₁₄ are each independentlyselected from the group consisting of hydrogen, deuterium, halogen, aC₆-C₆₀ aryl group, a fluorenyl group, a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from O, N, S, Si, and P,-L-N(R′)(R″), a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₁-C₃₀alkoxy group, and a C₆-C₃₀ aryloxy group.

R₂₁ and R₂₂ i) are each independently selected from the group consistingof hydrogen, a C₆-C₆₀ aryl group, a fluorenyl group, a fused ring groupof a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring, a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from O,N, S, Si, and P, and -L-N(R′)(R″), or ii) are linked together to form amonocyclic or polycyclic ring.

However, only when R₂₁ and R₂₂ are linked together to form a ring, R₁ toR₄ and R₁₁ to R₁₄ all may be hydrogen at the same time. In cases otherthan the case where R₂₁ and R₂₂ are linked together to form a ring, atleast one of R₁ to R₄ is not hydrogen, and at the same time, at leastone of R₁₁ to R₁₄ is not hydrogen.

A ring formed by linkage of R₂₁ and R₂₂ not only may be an aromatic ringor a hetero ring containing at least one heteroatom, but may also take aform in which an aromatic ring and an aliphatic ring are fused. By wayof example, R₂₁ and R₂₂ may be linked together to form an aromatic ringsuch as benzene, naphthalene, or phenanthrene, wherein the formedaromatic ring may have 6 to 60 nuclear carbon atoms. Also, R₂₁ and R₂₂may be linked together to form a hetero ring such as thiophene, furan,pyridine, indole, or quinoline, wherein the formed hetero ring may have2 to 60 nuclear carbon atoms. Further, in the case of a polycyclic ring,it may be a fused polycyclic ring, a non-fused polycyclic ring in whicha plurality of cycles are not fused, or a mixed polycyclic ring in whicha fused polycyclic ring and a non-fused polycyclic ring are mixed.

In Formula 1 above, X and Y are each independently S, O, or SiR₃₁R₃₂.Here, R₃₁ and R₃₂ may be each independently hydrogen, a C₆-C₆₀ arylgroup, a C₂-C₆₀ heterocyclic group containing at least one heteroatomselected from O, N, S, Si, and P, or a C₁-C₅₀ alkyl group. In the aboveFormula, m and n are each 0 or 1, with the proviso that the case whereboth m and n are 0 is excluded. Since m+n is an integer equal to orgreater than 1, at least one of X and Y has to exist.

L is selected from the group consisting of a single bond; a C₆-C₆₀arylene group; a fluorenylene group; a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from O, N, S, Si, and P; anda bivalent aliphatic hydrocarbon group. Here, the arylene group, thefluorenyl group, the heterocyclic group, and the aliphatic hydrocarbongroup may be substituted by one or more substituents selected from thegroup consisting of a nitro group, a cyano group, a halogen group, aC₁-C₂₀ alkyl group, a C₆-C₂₀ aryl group, a C₂-C₂₀ heterocyclic group, aC₁-C₂₀ alkoxy group, and an amino group.

Ar is selected from the group consisting of a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from O, N, S, Si, and P, aC₆-C₆₀ aryl group, or —N(R′)(R″). and R′ and R″ defined in thedescription of R₁ to R₄ and R₁₁ to R₁₄, R₂₁, R₂₂, Ar, and the like maybe each independently a C₂-C₆₀ heterocyclic group containing at leastone heteroatom selected from O, N, S, Si, and P, a C₆-C₂₀ aryl group, ora fluorenyl group.

Preferably, Ar may be a compound represented by Formula 1a below.

In Formula 1a, X₅ to X₇ are each independently nitrogen or C(R₅₁ withthe proviso that at least one of X₅ to X₇ is N, preferably two of X₅ toX₇ are nitrogen (N), wherein R₅₁ is selected from the group consistingof a C₂-C₂₀ alkyl group, a C₆-C₂₀ aryl group, a C₂-C₂₀ alkenyl group, aC₂-C₆₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P; and

Ar₅ and Ar₆ are different from each other and each independentlyselected from the group consisting of a substituted or unsubstitutedC₆-C₆₀ aryl group, a substituted or unsubstituted fluorenyl group, asubstituted or unsubstituted C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, accordingly the compound represented by the Formula 1a above maybe asymmetric structure.

Preferably, Ar₅ and Ar₆ are each independently C₆-C₃₀ aryl group,fluorenyl group, C₂-C₃₀ heterocyclic group, and as examples, phenyl,naphthyl, biphenyl, 9,9-dimethyl fluorenyl, 9,9-diphenyl fluorenyldibenzofuranyl, dibenzothiophenyl, carbazolyl. More preferably, at leastone of Ar₅ and Ar₆ is naphthyl.

Preferably, Ar₅ and Ar₆ may be optionally substituted by one or moresubstituents selected from the group consisting of a nitro group, acyano group, a halogen group, a C₁-C₂₀ alkyl group, a C₆-C₂₀ aryl group,a C₂-C₂₀ heterocyclic group, a C₁-C₂₀ alkoxy group, and an amino group.

R′ and R″ defined in the description of R₁ to R₄ and R₁₁ to R₁₄, R₂₁,Ar, and the like may be each independently a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from O, N, S, Si, and P, aC₆-C₂₀ aryl group, or a fluorenyl group.

R₁ to R₄, R₁₁ to R₁₄, R₂₁, R₂₂, a ring formed by R₂₁ and R₂₂, R₃₁, R₃₂,R₅₁, Ar, R′, R″ may be substituted by one or more substituents selectedfrom the group consisting of deuterium, halogen, a silane group, a borongroup, a germanium group, a cyano group, a nitro group, a C₁-C₂₀alkylthio group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀aryl group substituted by deuterium, a C₂-C₂₀ heterocyclic group, aC₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀ arylalkenyl group.

For example, when R₁ to R₄, R₁₁ to R₁₄, R₂₁, R₂₂, a ring formed by R₂₁and R₂₂, R₃₁, R₃₂, R₅₁, Ar, R′, and R″ are an aryl group, the aryl groupmay be substituted by one or more substituents selected from the groupconsisting of deuterium, halogen, a silane group, a boron group, agermanium group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group,a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, aC₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl groupsubstituted by deuterium, a C₂-C₂₀ heterocyclic group, a C₃-C₂₀cycloalkyl group, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀ aryl alkenylgroup.

When R₁ to R₄, R₁₁ to R₁₄, R₂₁, R₂₂, a ring formed by R₂₁ and R₂₂, R₃₁,R₃₂, R₅₁, Ar, R′, and R″ are a heterocyclic group, the heterocyclicgroup may be substituted by one or more substituents selected from thegroup consisting of deuterium, halogen, a silane group, a cyano group, anitro group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀alkenyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted bydeuterium, a C₂-C₂₀ heterocyclic group, a C₃-C₂₀ cycloalkyl group, aC₇-C₂₀ aryl alkyl group, and a C₈-C₂₀ aryl alkenyl group.

When R₁ to R₄, R₁₁ to R₁₄, R₂₁, R₂₂, a ring formed by R₂₁ and R₂₂, R′,and R″ are a fluorenyl group, the fluorenyl group may be substituted byone or more substituents selected from the group consisting ofdeuterium, halogen, a silane group, a cyano group, a C₁-C₂₀ alkyl group,a C₂-C₂₀ alkenyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl groupsubstituted by deuterium, a C₂-C₂₀ heterocyclic group, and a C₃-C₂₀cycloalkyl group.

When R₁ to R₄, R₁₁ to R₁₄, R₂₁, R₂₂, and a ring formed by R₂₁ and R₂₂,are a fused ring group, the fused ring group may be substituted by oneor more substituents selected from the group consisting of deuterium,halogen, a silane group, a boron group, a germanium group, a cyanogroup, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, aC₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, aC₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, aC₂-C₂₀ heterocyclic group, a C₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkylgroup, and a C₈-C₂₀ arylalkenyl group.

When R₁ to R₄, R₁₁ to R₁₄, R₃₁, R₃₂ and R₅₁ are an alkyl group, thealkyl group may be substituted by one or more substituents selected fromthe group consisting of halogen, a silane group, a boron group, a cyanogroup, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenylgroup, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted bydeuterium, a C₂-C₂₀ heterocyclic group, a C₇-C₂₀ arylalkyl group, and aC₈-C₂₀ arylalkenyl group.

When R₁ to R₄, R₁₁ to R₁₄ and R₅₁ are an alkenyl group, the alkenylgroup may be substituted by one or more substituents selected from thegroup consisting of deuterium, halogen, a silane group, a cyano group, aC₁-C₂₀ alkoxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, aC₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, aC₂-C₂₀ heterocyclic group, a C₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkylgroup, and a C₈-C₂₀ arylalkenyl group.

When R₁ to R₄ and R₁₁ to R₁₄ are an alkoxy group, the alkoxy group maybe substituted by one or more substituents selected from the groupconsisting of deuterium, halogen, a silane group, a C₁-C₂₀ alkyl group,a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, aC₂-C₂₀ heterocyclic group, and a C₃-C₂₀ cycloalkyl group.

When R₁ to R₄ and R₁₁ to R₁₄ are an aryloxy group, the aryloxy group maybe substituted by one or more substituents selected from the groupconsisting of deuterium, a silane group, a cyano group, a C₁-C₂₀ alkylgroup, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted bydeuterium, a C₂-C₂₀ heterocyclic group, and a C₃-C₂₀ cycloalkyl group.

The compound represented by Formula 1 above may be represented by one ofFormulas below.

In Formulas 2 to 9 above, Ar′ is selected from the group consisting ofhydrogen, deuterium, a halogen group, a C₁-C₂₀ alkyl group, a C₂-C₂₀alkenyl group, a C₁-C₂₀ alkoxy group, -L-N(R′)(R″), a C₆-C₂₀ aryl group,a C₆-C₂₀ aryl group substituted by deuterium, a C₇-C₂₀ arylalkyl group,a C₈-C₂₀ arylalkenyl group, a C₂-C₂₀ heterocyclic group, a nitrilegroup, and an acetylene group.

X₁-X₄ are CR₄₁ or N, wherein R₄₁ may be hydrogen, deuterium, a C₆-C₂₀aryl group, or a C₂-C₂₀ heterocyclic group, and R₁ to R₄, R₁₁ to R₁₄,R₂₁, R₂₂, R′, R″, X, Y, L, Ar, Ar₅, Ar₆, and X₅ to X₇ are as defined inFormula 1 above.

In Formulas 10 to 13, R₁ to R₄, R₁₁ to R₁₄, R₂₁, R₂₂, X, Y and L are thesame as defined in Formula 1, and Ar₅, Ar₆, and X₅ to X₇ are the same asdefined in Formula 1a above.

More specially, the compound represented by Formula 1 above may be oneof compounds below.

Hereinafter, Synthesis Examples of the inventive compound represented byFormula 1 above and Preparation Examples of an organic electric elementwill be described in detail by way of example. However, the followingexamples are only for illustrative purposes and are not intended tolimit the scope of the invention.

SYNTHESIS EXAMPLE

By way of example, the inventive compound is prepared by reacting one ofSub 1 to Sub 4 with Sub 5, as represented in Reaction Scheme 1 below. Inthe following Reaction Schemes, R₁ corresponds to one of R₁ to R₄ inFormula 1, R₂ corresponds to R₂₁ or R₂₂ in Formula 1, and R₃ correspondsto one of R₁₁ to R₁₄ in Formula 1.

By way of example, the inventive compound may be prepared by ReactionScheme 1 or Reaction Scheme 2 below.

Method 1

Hereinafter, synthesis methods of Sub 1 to Sub 4, Sub 6, Sub 7, Sub 12,and Sub 13 and then preparation methods of the inventive compoundaccording to Reaction Schemes above will be described.

1. Synthesis of Sub 1-4, 6-7 and 12-13 Synthesis Example of Sub 1

Synthesis Method of Sub 1-1

After a dibenzothiophene derivative substituted by R₁, R₂ was dissolvedin a carbon disulfide solvent under a nitrogen atmosphere, bromine wasslowly added dropwise to the reactants, followed by stirring at roomtemperature for 12 hours.

Upon completion of the reaction, the organic solvent was concentratedusing a vacuum apparatus, and the resultant product was recrystallizedusing an ethanol solvent to obtain desired Sub 1-1.

Synthesis Method of Sub 1-2

Sub 1-1 obtained above was dissolved in anhydrous THF, the temperatureof the reactants was lowered to −78° C., n-BuLi (2.5M in hexane) wasslowly added dropwise to the reactants, and then the reactants werestirred at 0° C. for 1 hour. The temperature of the reactants waslowered to −78° C. again, and trimethyl borate was added dropwise to thereactants, followed by stirring at room temperature for 12 hours. Uponcompletion of the reaction, the reaction product was added with a 2N-HClaqueous solution, was stirred for 30 minutes, and then was extractedwith ether. The extracted organic layer was dried with MgSO₄ andconcentrated, and then the produced organic material was separated by asilica gel column and recrystallization to obtain desired Sub 1-2.

Synthesis Method of Sub 1-3

Sub 1-2 obtained above, 1-bromo-2-nitrobenzene substituted by R₃,Pd(PPh₃)₄, and K₂CO₃ were dissolved in anhydrous THF and a small amountof water, followed by reflux for 24 hours. Upon completion of thereaction, the temperature of the reaction product was lowered to roomtemperature, the reaction product was extracted with CH₂Cl₂, and waswashed with water. The extracted organic layer was dried with MgSO₄ andconcentrated, and then the produced organic material was separated by asilica gel column to obtain desired Sub 1-3.

Synthesis Method of Sub 1

Sub 1-3 obtained above and triphenyl phosphine were dissolved ino-dichlorobenzene, followed by reflux for 24 hours. Upon completion ofthe reaction, the solvent was removed using vacuum distillation, andthen the concentrated product was separated by a silica gel column andrecrystallization to obtain desired Sub 1.

Synthesis Example of Sub 2

Synthesis Method of Sub 2-1

Except that 4-bromophenylboronic acid substituted by R₂,(2-iodophenyl)(methyl)sulfane substituted by R₁, Pd(PPh₃)₄, out toobtain desired Sub 2-1.

Synthesis Method of Sub 2-2

Sub 2-1 was dissolved in acetic acid, and hydrogen peroxide dissolved inacetic acid was added dropwise to the reactants, followed by stirring atroom temperature for 6 hours. Upon completion of the reaction, aceticacid was removed using a vacuum apparatus, and the resultant product wasseparated by a silica gel column to obtain desired Sub 2-2.

Synthesis Method of Sub 2-3

Sub 2-3 obtained above and trifluoromethane sulfonic acid were mixed,the mixture was stirred at room temperature for 24 hours, and water andpyridine (8:1) were slowly added to the mixture, followed by reflux for30 minutes. Upon completion of the reaction, the temperature of thereaction product was lowered, the reaction product was extracted withCH₂Cl₂, and was washed with water. A small amount of water was removedfrom the extract by anhydrous MgSO₄, the extract was subjected tovacuum-filtration, and then the filtrated organic solvent wasconcentrated. The resultant product was separated by a silica gel columnand recrystallizationo to obtain desired Sub 2-3.

Synthesis Method of Sub 2-4

Except that Sub 2-3 obtained above was used instead of Sub 1-1, the sameprocedure as described in Synthesis Method of Sub 1-2 was carried out toobtain desired Sub 2-4.

Synthesis Method of Sub 2-5

Except that Sub 2-4 obtained above, 1-bromo-2-nitrobenzene substitutedby R₃, Pd(PPh₃)₄, K₂CO₃, THF, and water were used as reactants, the sameprocedure as described in Synthesis Method of Sub 1-3 was carried out toobtain desired Sub 2-5.

Synthesis Method of Sub 2

Except that Sub 2-5 obtained above was used instead of Sub 1-3, the sameprocedure as described in Synthesis Method of Sub 1 was carried out toobtain desired Sub 2.

Synthesis Example of Sub 3

Synthesis Method of Sub 3-1

Except that 5-bromobenzo[b]naphtha[2,1-d]thiophene was used instead ofSub 1-1, the same procedure as described in Synthesis Method of Sub 1-2was carried out to obtain desired Sub 3-1.

Synthesis Method of Sub 3-2

Except that Sub 3-1 obtained above, 1-bromo-2-nitrobenzene substitutedby R₃, Pd(PPh₃)₄, K₂CO₃, THF, and water were used as reactants, the sameprocedure as described in Synthesis Method of Sub 1-3 was carried out toobtain desired Sub 3-2.

Synthesis Method of Sub 3

Except that Sub 3-2 obtained above was used instead of Sub 1-3, the sameprocedure as described in Synthesis Method of Sub 1 was carried out toobtain desired Sub 3.

Synthesis Example of Sub 4

Synthesis Method of Sub 4-1

Except that 4-bromonaphthalen-1-ylboronic acid,(2-bromophenyl)(methyl)sulfane substituted by R₁, Pd(PPh₃)₄, K₂CO₃, THF,and water were used as reactants, the same procedure as described inSynthesis Method of Sub 1-3 was carried out to obtain desired Sub 4-1.

Synthesis Method of Sub 4-2

Except that Sub 4-1 obtained above was used instead of Sub 2-1, the sameprocedure as described in Synthesis Method of Sub 2-2 was carried out toobtain desired Sub 4-2.

Synthesis Method of Sub 4-3

Except that Sub 4-2 obtained above was used instead of Sub 2-2, the sameprocedure as described in Synthesis Method of Sub 2-3 was carried out toobtain desired Sub 4-3.

Synthesis Method of Sub 4-4

Except that Sub 4-3 obtained above was used instead of Sub 1-1, the sameprocedure as described in Synthesis Method of Sub 1-2 was carried out toobtain desired Sub 4-4.

Synthesis Method of Sub 4-5

Except that Sub 4-4 obtained above, 1-bromo-2-nitrobenzene substitutedby R₃, Pd(PPh₃)₄, K₂CO₃, THF, and water were used as reactants, the sameprocedure as described in Synthesis Method of Sub 1-3 was carried out toobtain desired Sub 4-5.

Synthesis Method of Sub 4

Except that Sub 4-5 obtained above was used instead of Sub 1-3, the sameprocedure as described in Synthesis Method of Sub 1 was carried out toobtain desired Sub 4.

Synthesis Example of Sub 6

Synthesis Method of Sub 6-1

To a solution of 1 equivalent of dibenzofuran derivatives substituted byR₁ and R₂ in the DMF(6.3 ml DMF/1 mmol of dibenzofurane) was addedBis(pinacolato)diboron (1.1 eq.), Pd(dppf)Cl₂ (0.03 eq.), KOAc(3 eq) andstirred at 90° C. After completion of the reaction, DMF was removed byvacuum distillation and then, the residue was extracted with CH₂Cl₂ andwater. The organic layer was dried with MgSO₄, and concentrated undervacuum. The resultant was separated by silica gel column andrecrystallization to obtain the Sub 6-1.

Synthesis Method of Sub 6-2

To a solution of Sub 6-1 (1 eq.) in THF (4.4 ml/1 mmol) was addedbromo-2-nitrobenzene(1 eq.) substituted by R₃, K₂CO₃ (3 eq),Pd(PPh₃)₄(0.03 eq), water (2.2 ml/1 mmol) and stirred at 95° C. Aftercompletion of the reaction, the reactant was extracted with CH₂Cl₂ andwater and dried with MgSO₄, concentrated under vacuum. The residue wasseparated by silica gel column to obtain the 6-2.

Synthesis Method of Sub 6

To a solution of Sub 6-2 (1 eq.) in o-dichlorobenzene (5 ml/1 mmol) wasadded triphenylphosphine (2.5 eq.) and stirred at 200° C. Aftercompletion of the reaction, o-dichlorobenzene was removed by vacuumdistillation, and the residue was extracted with CH₂Cl₂ and water anddried with MgSO₄, concentrated under vacuum. The residue was separatedby silica gel column and recrystallization to obtain the 6.

Synthesis Example of Sub 7

Synthesis Method of Sub 7-1

Sub 7-1 was prepared from dibenzofuran derivatives substituted by R₁(1eq.), DMF (6.3 ml/1 mmol), Bis(pinacolato)diboron (1.1 eq), Pd(dppf)Cl₂(0.03 eq), KOAc(3 eq) according to the same way used for Sub 6-1 above.

Synthesis Method of Sub 7-2

Sub 7-2 was prepared from Sub 7-1 (1 eq.), THF (4.4 ml/1 mmol of sub7-1), bromo-2-nitrobenzene derivatives substituted by R₃(1 eq.), K₂CO₃(3 eq), Pd(PPh₃)₄(0.03 eq), water (2.2 ml/1 mmol of sub 7-1) accordingto the same way used for Sub 6-2 above.

Synthesis Method of Sub 7

Sub 7 was prepared from Sub 7-2 (1 eq.), o-dichlorobenzene (5 ml/1 mmolof Sub 7-2), triphenylphosphine (2.5 eq.) according to the same way usedfor Sub 6 above.

Synthesis Example of Sub 12

Synthesis Method of Sub 12-1

Sub 12-1 was prepared from dibenzofuran derivatives substituted by R₁(1eq.), DMF (6.3 ml/1 mmol), Bis(pinacolato)diboron (1.1 eq), Pd(dppf)Cl₂(0.03 eq), KOAc(3 eq) according to the same way used for Sub 6-1 above.

Synthesis Method of Sub 12-2

Sub 12-2 was prepared from Sub 12-1 (1 eq.), THF (4.4 ml/1 mmol of sub7-1), bromo-2-nitrobenzene derivatives substituted by R₃(1 eq.), K₂CO₃(3 eq), Pd(PPh₃)₄(0.03 eq), water (2.2 ml/1 mmol of sub 7-1) accordingto the same way used for Sub 6-2 above.

Synthesis Method of Sub 12

Sub 12 was prepared from Sub 12-2 (1 eq.), o-dichlorobenzene (5 ml/1mmol of Sub 7-2), triphenylphosphine (2.5 eq.) according to the same wayused for Sub 6 above.

Synthesis Example of Sub 13

Synthesis Method of Sub 13-1

Sub 13-1 was prepared from dibenzofuran derivatives substituted by R₁(1eq.), DMF (6.3 ml/1 mmol), Bis(pinacolato)diboron (1.1 eq), Pd(dppf)Cl₂(0.03 eq), KOAc(3 eq) according to the same way used for Sub 6-1 above.

Synthesis Method of Sub 13-2

Sub 7-2 was prepared from Sub 13-1 (1 eq.), THF (4.4 ml/1 mmol of sub13-1), bromo-2-nitrobenzene derivatives substituted by R₃(1 eq.), K₂CO₃(3 eq), Pd(PPh₃)₄(0.03 eq), water (2.2 ml/1 mmol of sub 13-1) accordingto the same way used for Sub 6-2 above.

Synthesis Method of Sub 13

Sub 13 was prepared from Sub 13-2 (1 eq.), o-dichlorobenzene (5 ml/1mmol of Sub 13-2), triphenylphosphine (2.5 eq.) according to the sameway used for Sub 6 above.

2. Sub 5 and Sub 8 Examples of Sub 5

Examples of Sub 5 include, but not limited to, the following materials.

Field desorption mass spectrometry (FD-MS) values for the abovematerials of Sub 5 above are given in Table 1 below.

TABLE 1 Compound FD-MS Compound FD-MS Sub 5-1 m/z = 203.94 (C₆H₅I =204.01) Sub 5-2 m/z = 253.96 (C₁₀H₇I = 254.07) Sub 5-3 m/z = 309.02(C₁₇H₁₂BrN = 310.19) Sub 5-4 m/z = 311.01 (C₁₅H₁₀BrN₃ = 312.16) Sub 5-5m/z = 310.01 (C₁₆H₁₁BrN₂ = 311.18) Sub 5-6 m/z = 310.01 (C₁₆H₁₁BrN₂ =311.18) Sub 5-7 m/z = 310.01 (C₁₆H₁₁BrN₂ = 311.18) Sub 5-8 m/z = 279.97(C₁₂H₉I = 280.10) Sub 5-9 m/z = 387.04 (C₂₁H₁₄BrN₃ = 388.26) Sub 5-10m/z = 386.04 (C₂₂H₁₅BrN₂ = 387.27) Sub 5-11 m/z = 386.04 (C₂₂H₁₅BrN₂ =387.27) Sub 5-12 m/z = 348.03 (C₁₉H₁₃BrN₂ = 349.22) Sub 5-13 m/z =271.99 (C₁₃H₉BrN₂ = 273.13) Sub 5-14 m/z = 283.99 (C₁₄H₉BrN₂ = 285.14)Sub 5-15 m/z = 289.03 (C₁₄H₄D₅BrN₂ = 290.17) Sub 5-16 m/z = 360.03(C₂₀H₁₃BrN₂ = 361.23) Sub 5-17 m/z = 360.03 (C₂₀H₁₃BrN₂ = 361.23) Sub5-18 m/z = 334.01 (C₁₈H₁₁BrN₂ = 335.20) Sub 5-19 m/z = 334.01(C₁₈H₁₁BrN₂ = 335.20) Sub 5-20 m/z = 436.06 (C₂₆H₁₇BrN₂ = 437.33) Sub5-21 m/z = 400.06 (C₂₃H₁₇BrN₂ = 401.30) Sub 5-22 m/z = 360.03(C₂₀H₁₃BrN₂ = 361.23) Sub 5-23 m/z = 365.06 (C₂₀H₈D₅BrN₂ = 366.27) Sub5-24 m/z = 436.06 (C₂₆H₁₇BrN₂ = 437.33) Sub 5-25 m/z = 436.06(C₂₆H₁₇BrN₂ = 437.33) Sub 5-26 m/z = 410.04 (C₂₄H₁₅BrN₂ = 411.29) Sub5-27 m/z = 410.04 (C₂₄H₁₅BrN₂ = 411.29) Sub 5-28 m/z = 512.09(C₃₂H₂₁BrN₂ = 513.43) Sub 5-29 m/z = 476.09 (C₂₉H₂₁BrN₂ = 477.39) Sub5-30 m/z = 360.03 (C₂₀H₁₃BrN₂ = 361.23) Sub 5-31 m/z = 365.06(C₂₀H₈D₅BrN₂ = 366.27) Sub 5-32 m/z = 436.06 (C₂₆H₁₇BrN₂ = 437.33) Sub5-33 m/z = 436.06 (C₂₆H₁₇BrN₂ = 437.33) Sub 5-34 m/z = 410.04(C₂₄H₁₅BrN₂ = 411.29) Sub 5-35 m/z = 410.04 (C₂₄H₁₅BrN₂ = 411.29) Sub5-36 m/z = 512.09 (C₃₂H₂₁BrN₂ = 513.43) Sub 5-37 m/z = 476.09(C₂₉H₂₁BrN₂ = 477.39) Sub 5-38 m/z = 284.99 (C₁₃H₈BrN₃ = 286.13) Sub5-39 m/z = 290.02 (C₁₃H₃D₅BrN₃ = 291.16) Sub 5-40 m/z = 361.02(C₁₉H₁₂BrN₃ = 362.22) Sub 5-41 m/z = 361.02 (C₁₉H₁₂BrN₃ = 362.22) Sub5-42 m/z = 335.01 (C₁₇H₁₀BrN₃ = 336.19) Sub 5-43 m/z = 335.01(C₁₇H₁₀BrN₃ = 336.19) Sub 5-44 m/z = 437.05 (C₂₅H₁₆BrN₃ = 438.32) Sub5-45 m/z = 401.05 (C₂₂H₁₆BrN₃ = 402.29) Sub 5-46 m/z = 361.02(C₁₉H₁₂BrN₃ = 362.22) Sub 5-47 m/z = 366.05 (C₁₉H₇D₅BrN₃ = 367.25) Sub5-48 m/z = 437.05 (C₂₅H₁₆BrN₃ = 438.32) Sub 5-49 m/z = 437.05(C₂₅H₁₆BrN₃ = 438.32) Sub 5-50 m/z = 411.04 (C₂₃H₁₄BrN₃ = 412.28) Sub5-51 m/z = 411.04 (C₂₃H₁₄BrN₃ = 412.28) Sub 5-52 m/z = 513.08(C₃₁H₂₀BrN₃ = 514.41) Sub 5-53 m/z = 477.08 (C₂₈H₂₀BrN₃ = 478.38) Sub5-54 m/z = 361.02 (C₁₉H₁₂BrN₃ = 362.22) Sub 5-55 m/z = 366.05(C₁₉H₇D₅BrN₃ = 367.25) Sub 5-56 m/z = 437.05 (C₂₅H₁₆BrN₃ = 438.32) Sub5-57 m/z = 437.05 (C₂₅H₁₆BrN₃ = 438.32) Sub 5-58 m/z = 411.04(C₂₃H₁₄BrN₃ = 412.28) Sub 5-59 m/z = 411.04 (C₂₃H₁₄BrN₃ = 412.28) Sub5-60 m/z = 513.08 (C₃₁H₂₀BrN₃ = 514.41) Sub 5-61 m/z = 477.08(C₂₈H₂₀BrN₃ = 478.38) Sub 5-62 m/z = 284.99 (C₁₃H₈BrN₃ = 286.13) Sub5-63 m/z = 290.02 (C₁₃H₃D₅BrN₃ = 291.16) Sub 5-64 m/z = 361.02(C₁₉H₁₂BrN₃ = 362.22) Sub 5-65 m/z = 361.02 (C₁₉H₁₂BrN₃ = 362.22) Sub5-66 m/z = 335.01 (C₁₇H₁₀BrN₃ = 336.19) Sub 5-67 m/z = 335.01(C₁₇H₁₀BrN₃ = 336.19) Sub 5-68 m/z = 437.05 (C₂₅H₁₆BrN₃ = 438.32) Sub5-69 m/z = 401.05 (C₂₂H₁₆BrN₃ = 402.29) Sub 5-70 m/z = 361.02(C₁₉H₁₂BrN₃ = 362.22) Sub 5-71 m/z = 366.05 (C₁₉H₇D₅BrN₃ = 367.25) Sub5-72 m/z = 437.05 (C₂₅H₁₆BrN₃ = 438.32) Sub 5-73 m/z = 437.05(C₂₅H₁₆BrN₃ = 438.32) Sub 5-74 m/z = 411.04 (C₂₃H₁₄BrN₃ = 412.28) Sub5-75 m/z = 411.04 (C₂₃H₁₄BrN₃ = 412.28) Sub 5-76 m/z = 513.08(C₃₁H₂₀BrN₃ = 514.41) Sub 5-77 m/z = 477.08 (C₂₈H₂₀BrN₃ = 478.38) Sub5-78 m/z = 361.02 (C₁₉H₁₂BrN₃ = 362.22) Sub 5-79 m/z = 366.05(C₁₉H₇D₅BrN₃ = 367.25) Sub 5-80 m/z = 437.05 (C₂₅H₁₆BrN₃ = 438.32) Sub5-81 m/z = 437.05 (C₂₅H₁₆BrN₃ = 438.32) Sub 5-82 m/z = 411.04(C₂₃H₁₄BrN₃ = 412.28) Sub 5-83 m/z = 411.04 (C₂₃H₁₄BrN₃ = 412.28) Sub5-84 m/z = 513.08 (C₃₁H₂₀BrN₃ = 514.41) Sub 5-85 m/z = 477.08(C₂₈H₂₀BrN₃ = 478.38)

Examples of Sub 8

Examples of Sub 8 include, but not limited to, the following materials

Field desorption mass spectrometry (FD-MS) values for the abovematerials of Sub 8 above are given in Table 1-1 below.

TABLE 1-1 Compound FD-MS Compound FD-MS Sub 8-1 m/z = 360.03 (C₂₀H₁₃BrN₂= 361.24) Sub 8-2 m/z = 360.03 (C₂₀H₁₃BrN₂ = 361.24) Sub 8-3 m/z =386.04 (C₂₂H₁₅BrN₂ = 387.28) Sub 8-4 m/z = 386.04 (C₂₂H₁₅BrN₂ = 387.28)Sub 8-5 m/z = 436.06 (C₂₆H₁₇BrN₂ = 437.34) Sub 8-6 m/z = 462.07(C₂₈H₁₉BrN₂ = 463.38) Sub 8-7 m/z = 450.04 (C₂₆H₁₅BrN₂O = 451.32) Sub8-8 m/z = 492.03 (C₂₈H₁₇BrN₂S = 493.42) Sub 8-9 m/z = 476.09 (C₂₉H₂₁BrN₂= 477.41) Sub 8-10 m/z = 551.10 (C₃₄H₂₂BrN₃ = 552.48) Sub 8-11 m/z =462.07 (C₂₈H₁₉BrN₂ = 463.38) Sub 8-12 m/z = 396.10 (C₂₂H₅D₁₀BrN₂ =397.34) Sub 8-13 m/z = 442.10 (C₂₆H₂₃BrN₂ = 443.39) Sub 8-14 m/z =492.03 (C₂₈H₁₇BrN₂S = 493.42) Sub 8-15 m/z = 512.09 (C₃₂H₂₁BrN₂ =513.44) Sub 8-16 m/z = 618.08 (C₃₈H₂₃BrN₂S = 619.58) Sub 8-17 m/z =416.00 (C₂₂H₁₃BrN₂S = 417.32) Sub 8-18 m/z = 361.02 (C₁₉H₁₂BrN₃ =362.23) Sub 8-19 m/z = 361.02 (C₁₉H₁₂BrN₃ = 362.23) Sub 8-20 m/z =387.04 (C₂₁H₁₄BrN₃ = 388.27) Sub 8-21 m/z = 387.04 (C₂₁H₁₄BrN₃ = 388.27)Sub 8-22 m/z = 437.05 (C₂₅H₁₆BrN₃ = 438.33) Sub 8-23 m/z = 463.07(C₂₇H₁₈BrN₃ = 464.37) Sub 8-24 m/z = 451.03 (C₂₅H₁₄BrN₃O = 452.31) Sub8-25 m/z = 493.02 (C₂₇H₁₆BrN₃S = 494.41) Sub 8-26 m/z = 477.08(C₂₈H₂₀BrN₃ = 478.39) Sub 8-27 m/z = 552.09 (C₃₃H₂₁BrN₄ = 553.46) Sub8-28 m/z = 397.10 (C₂₁H₄D₁₀BrN₃ = 398.33) Sub 8-29 m/z = 493.02(C₂₇H₁₆BrN₃S = 494.41) Sub 8-30 m/z = 513.08 (C₃₁H₂₀BrN₃ = 514.43) Sub8-31 m/z = 619.07 (C₃₇H₂₂BrN₃S = 620.57) Sub 8-32 m/z = 569.06(C₃₃H₂₀BrN₃S = 570.51)

3. Sub 9 and Sub 10 Examples of Sub 9

Examples of Sub 9 include, but not limited to, the following materials.

Examples of Sub 10

Examples of Sub 10 include, but not limited to, the following materials.

FD-MS values for the above materials of Sub 9 and Sub 10 are given inTable 2 below.

TABLE 2 Compound FD-MS Compound FD-MS Sub 9-1 m/z = 122.05 (C₆H₇BO₂ =121.93) Sub 9-2 m/z = 172.07 (C₁₀H₉BO₂ = 171.99) Sub 9-3 m/z = 172.07(C₁₀H₉BO₂ = 171.99) Sub 9-4 m/z = 123.05 (C₅H₆BNO₂ = 122.92) Sub 9-5 m/z= 289.13 (C₁₈H₁₆BNO₂ = 289.14) Sub 9-6 m/z = 339.14 (C₂₂H₁₈BNO₂ =339.19) Sub 9-7 m/z = 365.16 (C₂₄H₂₀BNO₂ = 365.23) Sub 9-8 m/z = 405.19(C₂₇H₂₄BNO₂ = 405.30) Sub 9-9 m/z = 405.19 (C₂₇H₂₄BNO₂ = 405.30) Sub10-1 m/z = 169.09 (C₁₂H₁₁N = 169.22) Sub 10-2 m/z = 245.12 (C₁₈H₁₅N =245.32) Sub 10-3 m/z = 219.10 (C₁₆H₁₃N = 219.28) Sub 10-4 m/z = 219.10(C₁₆H₁₃N = 219.28) Sub 10-5 m/z = 285.15 (C₂₁H₁₉N = 285.38) Sub 10-6 m/z= 321.15 (C₂₄H₁₉N = 321.41) Sub 10-7 m/z = 409.18 (C₃₁H₂₃N = 409.52) Sub10-8 m/z = 269.12 (C₂₀H₁₅N = 269.34) Sub 10-9 m/z = 269.12 (C₂₀H₁₅N =269.34) Sub 10-10 m/z = 295.14 (C₂₂H₁₇N = 295.38) Sub 10-11 m/z = 335.17(C₂₅H₂₁N = 335.44) Sub 10-12 m/z = 459.20 (C₃₅H₂₅N = 459.58)

4. Synthesis Example of Product

The compound according to the present invention may be synthesized byReaction Schemes 1 and 2 above. Examples of synthesizing the inventivecompound by these two methods are as follows.

Method 1 (Reaction Scheme 1)

Sub 1-4 and Sub 5 were mixed with toluene, and Pd₂(dba)₃, P(t-Bu)₃, andNaOt-Bu were added to the mixture respectively, followed by reflux understirring at 100° C. for 24 hours. The reaction product was extractedwith ether and water, the extracted organic layer was dried with MgSO₄and concentrated, and then the produced organic material was separatedby a silica gel column and recrystallized to obtain a final product.

Method 2 (Reaction Scheme 2)

[Method 2-1]

Compound Sub 11-1 or Sub 11-2 (1 equivalent weight) and THF were putinto a round bottom flask to dissolve the compound in THF, and compoundSub 9 (1.2 equivalent weight), Pd(PPh₃)₄(0.03 equivalent weight), NaOH(3 equivalent weight), and water were added to the reactants, followedby reflux under stirring. Upon completion of the reaction, the reactionproduct was extracted with ether and water, the extracted organic layerwas dried with MgSO₄ and concentrated, and then the produced organicmaterial was separated by a silica gel column and recrystallization toobtain a final product.

[Method 2-2]

Compound Sub 11-1 or Sub 11-2 (1 equivalent weight), compound Sub 10(1.2 equivalent weight), Pd₂(dba)₃ (0.05 equivalent weight), P(t-Bu)₃(0.1 equivalent weight), NaOt-Bu (3 equivalent weight), and toluene(10.5 mL/1 mmol) were put into a round bottom flask, and then thereactants were subjected to the reaction at 100° C. Upon completion ofthe reaction, the reaction product was extracted with ether and water,the extracted organic layer was dried with MgSO₄ and concentrated, andthen the produced organic material was separated by a silica gel columnand recrystallization to obtain a final product.

Examples of Sub 5, Sub 8 to Sub 10 used in Method 1 and Method 2include, but not limited to, the following compounds.

Synthesis Example of Product 1-1[Method 1]

A five-membered heterocyclic compound (7.1 g, 20 mmol) and2-bromo-4,6-diphenyl-1,3,5-triazine (7.5 g, 24 mmol) were mixed withtoluene (210 mL), and Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2mmol), and NaOt-Bu (5.8 g, 60 mmol) were added to the mixturerespectively, followed by reflux under stirring at 100° C. for 24 hours.The reaction product was extracted with methylene chloride and water,the extracted organic layer was dried with MgSO₄ and concentrated, andthen the produced organic material was separated by a silica gel columnand recrystallized to obtain 8.0 g of product 1-1 (yield 68%).

Synthesis Example of Product 1-13[Method 1]

Using a five-membered heterocyclic compound (8.5 g, 20 mmol),2-bromo-4,6-diphenyl-1,3,5-triazine (7.5 g, 24 mmol), toluene (210 mL),Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8g, 60 mmol), the same procedure as described in the synthesis method ofproduct 1-1 was carried out to obtain 8.4 g of product 1-13 (yield 64%).

Synthesis Example of Product 2-18[Method 1]

Using a five-membered heterocyclic compound (11 g, 20 mmol),bromobenzene (7.5 g, 24 mmol), toluene (210 mL), Pd₂(dba)₃ (0.92 g, 1mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8 g, 60 mmol), the sameprocedure as described in the synthesis method of product 1-1 wascarried out to obtain 9.7 g of product 2-18 (yield 62%).

Synthesis Example of Product 2-31[Method 1]

Using a five-membered heterocyclic compound (8.5 g, 20 mmol),4-(4-bromophenyl)-2,6-diphenylpyrimidine (9.3 g, 24 mmol), toluene (210mL), Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu(5.8 g, 60 mmol), the same procedure as described in the synthesismethod of product 1-1 was carried out to obtain 9.2 g of product 2-31(yield 63%).

Synthesis Example of Product 3-7[Method 1]

Using a five-membered heterocyclic compound (8.6 g, 20 mmol),2-bromo-4,6-diphenyl-1,3,5-triazine (7.5 g, 24 mmol), toluene (210 mL),Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8g, 60 mmol), the same procedure as described in the synthesis method ofproduct 1-1 was carried out to obtain 8.5 g of product 3-7 (yield 64%).

Synthesis Example of Product 3-12[Method 1]

Using a five-membered heterocyclic compound (9.1 g, 20 mmol),2-bromo-4,6-diphenyl-1,3,5-triazine (7.5 g, 24 mmol), toluene (210 mL),Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8g, 60 mmol), the same procedure as described in the synthesis method ofproduct 1-1 was carried out to obtain 8.5 g of product 3-12 (yield 62%).

Synthesis Example of Product 4-19[Method 1]

Using a five-membered heterocyclic compound (9.5 g, 20 mmol),4-bromobiphenyl(5.6 g, 24 mmol), toluene (210 mL), Pd₂(dba)₃ (0.92 g, 1mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8 g, 60 mmol), the sameprocedure as described in the synthesis method of product 1-1 wascarried out to obtain 8.2 g of product 4-19 (yield 65%).

Synthesis Example of Product 4-27[Method 1]

Using a five-membered heterocyclic compound (9.5 g, 20 mmol),2-(4-bromophenyl)imidazol[1,2-a]pyridine (6.6 g, 24 mmol), toluene (210mL), Pd₂(dba)₃ (0.92 g, 1mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu(5.8 g, 60 mmol), the same procedure as described in the synthesismethod of product 1-1 was carried out to obtain 8.1 g of product 4-27(yield 61%).

Synthesis Example of Product 3-28[Method 1]

Using a five-membered heterocyclic compound (6.5 g, 20 mmol),2-bromo-4-phenylquinazoline (6.8 g, 24 mmol), toluene (210 mL),Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8g, 60 mmol), the same procedure as described in the synthesis method ofproduct 1-1 was carried out to obtain 7.2 g of product 3-28 (yield 68%).

Synthesis Example of Product 3-38[Method 1]

Using a five-membered heterocyclic compound (6.5 g, 20 mmol),2-bromo-4-phenylquinazoline (10.5 g, 24 mmol), toluene (210 mL),Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8g, 60 mmol), the same procedure as described in the synthesis method ofproduct 1-1 was carried out to obtain 8.7 g of product 3-38 (yield 64%).

Synthesis Example of Product 3-44[Method 1]

Using a five-membered heterocyclic compound (6.5 g, 20 mmol),2-(3-bromophenyl)-4-phenylquinazoline (8.7 g, 24 mmol), toluene (210mL), Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu(5.8 g, 60 mmol), the same procedure as described in the synthesismethod of product 1-1 was carried out to obtain 7.4 g of product 3-44(yield 61%).

Synthesis Example of Product 4-28[Method 1]

Using a five-membered heterocyclic compound (6.5 g, 20 mmol),2-bromo-4-phenylquinazoline (6.8 g, 24 mmol), toluene (210 mL),Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8g, 60 mmol), the same procedure as described in the synthesis method ofproduct 1-1 was carried out to obtain 7.1 g of product 4-28 (yield 67%).

Synthesis Example of Product 6-1[Method 1]

Using a five-membered heterocyclic compound (6.5 g, 20 mmol),2-bromo-4-phenylpyrido[2,3-d]pyrimidine (6.9 g, 24 mmol), toluene (210mL), Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu(5.8 g, 60 mmol), the same procedure as described in the synthesismethod of product 1-1 was carried out to obtain 6.7 g of product 6-1(yield 63%).

Synthesis Example of Product 7-4[Method 1]

Using a five-membered heterocyclic compound (6.5 g, 20 mmol),4-([1,1′-biphenyl]-3-yl)-2-bromopyrido[3,2-d]pyrimidine (8.7 g, 24mmol), toluene (210 mL), Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2mmol), and NaOt-Bu (5.8 g, 60 mmol), the same procedure as described inthe synthesis method of product 1-1 was carried out to obtain 7.5 g ofproduct 7-4 (yield 62%).

Synthesis Example of Product 5-14[Method 2-1]

A five-membered heterocyclic compound (10.1 g, 20 mmol) and(4-(naphthalene-1-yl(phenyl)amino)phenyl)boronic acid (8.14 g, 24 mmol)were dissolved in THF, and Pd(PPh₃)₄(0.7 g, 0.6 mmol), NaOH (2.4 g, 60mmol), and water were added to the reactants, followed by reflux understirring. Upon completion of the reaction, the reaction product wasextracted with ether and water, the extracted organic layer was driedwith MgSO₄ and concentrated, and then the produced organic material wasseparated by a silica gel column and recrystallized to obtain 8.9 g ofproduct 5-14 (yield 62%).

Synthesis Example of Product 5-23[Method 2-1]

Using a five-membered heterocyclic compound (10.1 g, 20 mmol),(4-((9,9-dimethyl-9H-fluoren-2-yl)(phenyl)amino)phenyl)boronic acid(9.73 g, 24 mmol), Pd(PPh₃)₄(0.7 g, 0.6 mmol), and NaOH (2.4 g, 60mmol), the same procedure as described in the synthesis method ofproduct 5-14 was carried out to obtain 9.4 g of product 5-23 (yield60%).

Synthesis Example of Product 5-49[Method 2-1]

Using a five-membered heterocyclic compound (11.1 g, 20 mmol),(4-([1,1′-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid (8.77 g, 24mmol), Pd(PPh₃)₄(0.7 g, 0.6 mmol), and NaOH (2.4 g, 60 mmol), the sameprocedure as described in the synthesis method of product 5-14 wascarried out to obtain 10 g of product 5-49 (yield 63%).

Synthesis Example of Product 5-5[Method 2-2]

Using Di([1,1′-biphenyl]-4-yl)amine (6.4 g, 20 mmol), a five-memberedheterocyclic compound (12.1 g, 24 mmol), toluene (210 mL), Pd₂(dba)₃(0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8 g, 60mmol), the same procedure as described in the synthesis method ofproduct 1-1 was carried out to obtain 9.39 g of product 5-5 (yield 63%).

Synthesis Example of Product 5-6[Method 2-2]

Using 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (5.7 g, 20 mmol), afive-membered heterocyclic compound (12.1 g, 24 mmol), toluene (210 mL),Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8g, 60 mmol), the same procedure as described in the synthesis method ofproduct 1-1 was carried out to obtain 8.8 g of product 5-6 (yield 62%).

Synthesis Example of Product 5-19[Method 2-2]

Using Di-1-naphtyl amine (5.4 g, 20 mmol), a five-membered heterocycliccompound (12.1 g, 24 mmol), toluene (210 mL), Pd₂(dba)₃ (0.92 g, 1mmol), P(t-Bu)₃ (0.4 g, 2 mmol), and NaOt-Bu (5.8 g, 60 mmol), the sameprocedure as described in the synthesis method of product 1-1 wascarried out to obtain 8.89 g of product 5-19 (yield 64%).

Synthesis Example of Product 8-2[Method 1]

To a solution of five-membered heterocyclic compound (8 g, 24.74 mmol)in toluene (260 mL) was added2-bromo-4-(naphthalen-2-yl)-6-phenylpyrimidine (8.94 g, 24.74 mmol),Pd₂(dba)₃ (0.68 g, 0.74 mmol), P(t-Bu)₃ (0.30 g, 1.48 mmol), NaOt-Bu(7.13 g, 74.21 mmol) and stirred at 100° C. After completion of thereaction, the reactant was extracted with CH₂Cl₂ and water and theorganic layer was dried over MgSO₄ and concentrated. The residue wasseparated by silica gel column and recrystallization to obtain theproduct 8-2(10.9 g, 73%).

Synthesis Example of Product 8-4[Method 1]

Product 8-4(10.59 g, 68%) was prepared from five-membered heterocycliccompound (8 g, 24.74 mmol), toluene (260 mL),4-([1,1′-biphenyl]-3-yl)-2-bromo-6-phenylpyrimidine (9.58 g, 24.74mmol), Pd₂(dba)₃ (0.68 g, 0.74 mmol), P(t-Bu)₃ (0.30 g, 1.48 mmol),NaOt-Bu (7.13 g, 74.21 mmol) according to the same way used for 8-2above.

Synthesis Example of Product 8-9[Method 1]

Product 8-9(9.82 g, 63%) was prepared from five-membered heterocycliccompound (7 g, 21.64 mmol), toluene (227 mL),2-bromo-4-(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalen-2-yl)pyrimidine(10.33 g, 21.64 mmol), Pd₂(dba)₃ (0.59 g, 0.65 mmol), P(t-Bu)₃ (0.23 g,1.30 mmol), NaOt-Bu (6.24 g, 64.93 mmol) according to the same way usedfor 8-2 above.

Synthesis Example of Product 8-10[Method 1]

Product 8-10(9.88 g, 67%) was prepared from five-membered heterocycliccompound (6 g, 18.55 mmol), toluene (195 mL),3-(6-([1,1′-biphenyl]-4-yl)-2-bromopyrimidin-4-yl)-9-phenyl-9H-carbazole(10.25 g, 18.55 mmol), Pd₂(dba)₃ (0.51 g, 0.56 mmol), P(t-Bu)₃ (0.23 g,1.11 mmol), NaOt-Bu (5.35 g, 55.66 mmol) according to the same way usedfor 8-2 above.

Synthesis Example of Product 8-14[Method 1]

Product 8-14(9.56 g, 70%) was prepared from five-membered heterocycliccompound (6 g, 18.55 mmol), toluene (195 mL),2-(4-bromophenyl)-4-(dibenzo[b,d]thiophen-2-yl)-6-phenylpyrimidine (9.15g, 18.55 mmol), Pd₂(dba)₃ (0.51 g, 0.56 mmol), P(t-Bu)₃ (0.23 g, 1.11mmol), NaOt-Bu (5.35 g, 55.66 mmol) according to the same way used for8-2 above.

Synthesis Example of Product 8-26[Method 1]

Product 8-26(9.44 g, 72%) was prepared from five-membered heterocycliccompound (6 g, 18.55 mmol), toluene (195 mL),2-([1,1′:3′,1″-terphenyl]-5′-yl)-4-bromo-6-phenyl-1,3,5-triazine (8.62g, 18.55 mmol), Pd₂(dba)₃ (0.51 g, 0.56 mmol), P(t-Bu)₃ (0.23 g, 1.11mmol), NaOt-Bu (5.35 g, 55.66 mmol)according to the same way used for8-2 above.

Synthesis Example of Product 8-31[Method 1]

Product 8-31(9.57 g, 69%) was prepared from five-membered heterocycliccompound (7 g, 21.64 mmol), toluene (227 mL),2-([1,1′-biphenyl]-4-yl-2′,3′,4′,5′,6′-d5)-4-bromo-6-(phenyl-d5)-1,3,5-triazine(8.62 g, 21.64 mmol), Pd₂(dba)₃ (0.59 g, 0.65 mmol), P(t-Bu)₃ (0.23 g,1.30 mmol), NaOt-Bu (6.24 g, 64.93 mmol) according to the same way usedfor 8-2 above.

Synthesis Example of Product 8-33[Method 1]

Product 8-33(10.65 g, 69%) was prepared from five-membered heterocycliccompound (7 g, 21.64 mmol), toluene (227 mL),2-(3′-bromo-[1,1′-biphenyl]-3-yl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine(11.13 g, 21.64 mmol), Pd₂(dba)₃ (0.59 g, 0.65 mmol), P(t-Bu)₃ (0.26 g,1.30 mmol), NaOt-Bu (6.24 g, 64.93 mmol) according to the same way usedfor 8-2 above.

Synthesis Example of Product 9-2[Method 1]

To a solution of five-membered heterocyclic compound (7 g, 21.64 mmol)in toluene (227 mL) was added2-bromo-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (7.84 g, 21.64mmol), Pd₂(dba)₃ (0.59 g, 0.65 mmol), P(t-Bu)₃ (0.26 g, 1.3 mmol),NaOt-Bu (6.24 g, 64.93 mmol) and stirred at 100° C. After completion ofthe reaction, the reactant was extracted with CH₂Cl₂ and water and theorganic layer was dried over MgSO₄ and concentrated. The residue wasseparated by silica gel column and recrystallization to obtain theproduct 9-2(9.29 g, 71%).

Synthesis Example of Product 9-3[Method 1]

Product 9-3(10.36 g, 76%) was prepared from five-membered heterocycliccompound (7 g, 21.64 mmol), toluene (mL),4-([1,1′-biphenyl]-4-yl)-2-bromo-6-phenylpyrimidine (8.38 g, 21.64mmol), Pd₂(dba)₃ (0.59 g, 0.65 mmol), P(t-Bu)₃ (0.26 g, 1.3 mmol),NaOt-Bu (6.24 g, 64.93 mmol) according to the same way used for 9-2above.

Synthesis Example of Product 9-8[Method 1]

Product 9-8(10.1 g, 74%) was prepared from five-membered heterocycliccompound (6 g, 18.55 mmol), toluene (195 mL),4-([1,1′-biphenyl]-4-yl)-2-bromo-6-(dibenzo[b,d]thiophen-2-yl)pyrimidine(9.15 g, 18.55 mmol), Pd₂(dba)₃ (0.51 g, 0.56 mmol), P(t-Bu)₃ (0.23 g,1.11 mmol), NaOt-Bu (5.35 g, 55.66 mmol) according to the same way usedfor 9-2 above.

Synthesis Example of Product 9-14[Method 1]

Product 9-14(10.51 g, 77%) was prepared from five-membered heterocycliccompound (6 g, 18.55 mmol), toluene (195 mL),2-(4-bromophenyl)-4-(dibenzo[b,d]thiophen-2-yl)-6-phenylpyrimidine (9.15g, 18.55 mmol), Pd₂(dba)₃ (0.51 g, 0.56 mmol), P(t-Bu)₃ (0.23 g, 1.11mmol), NaOt-Bu (5.35 g, 55.66 mmol) according to the same way used for9-2 above.

Synthesis Example of Product 9-21[Method 1]

Product 9-21(8.86 g, 79%) was prepared from five-membered heterocycliccompound (6 g, 18.55 mmol), toluene (195 mL),2-bromo-4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazine (6.72 g, 18.55mmol), Pd₂(dba)₃ (0.51 g, 0.56 mmol), P(t-Bu)₃ (0.23 g, 1.11 mmol),NaOt-Bu (5.35 g, 55.66 mmol) according to the same way used for 9-2above.

Synthesis Example of Product 9-27[Method 1]

Product 9-27(9.28 g, 72%) was prepared from five-membered heterocycliccompound (6 g, 18.55 mmol), toluene (195 mL),2-bromo-4-(dibenzo[b,d]furan-4-yl)-6-(naphthalen-1-yl)-1,3,5-triazine(8.39 g, 18.55 mmol), Pd₂(dba)₃ (0.51 g, 0.56 mmol), P(t-Bu)₃ (0.23 g,1.11 mmol), NaOt-Bu (5.35 g, 55.66 mmol) according to the same way usedfor 9-2 above.

Synthesis Example of Product 9-30[Method 1]

Product 9-30(10.04 g, 68%) was prepared from five-membered heterocycliccompound (6 g, 18.55 mmol), toluene (195 mL),3-(4-([1,1′-biphenyl]-4-yl)-6-bromo-1,3,5-triazin-2-yl)-9-phenyl-9H-carbazole(10.27 g, 18.55 mmol), Pd₂(dba)₃ (0.51 g, 0.56 mmol), P(t-Bu)₃ (0.23 g,1.11 mmol), NaOt-Bu (5.35 g, 55.66 mmol) according to the same way usedfor 9-2 above.

Synthesis Example of Product 9-34[Method 1]

Product 9-34(10.09 g, 63%) was prepared from five-membered heterocycliccompound (6 g, 18.55 mmol), toluene (195 mL),2-([1,1′-biphenyl]-4-yl)-4-(8-bromodibenzo[b,d]thiophen-3-yl)-6-(naphthalen-1-yl)-1,3,5-triazine(11.51 g, 18.55 mmol), Pd₂(dba)₃ (0.51 g, 0.56 mmol), P(t-Bu)₃ (0.23 g,1.11 mmol), NaOt-Bu (5.35 g, 55.66 mmol) according to the same way usedfor 9-2 above.

Synthesis Example of Product 9-36[Method 1]

Product 9-36(10.9 g, 66%) was prepared from five-membered heterocycliccompound (10 g, 18.23 mmol), toluene (191 mL),2-bromo-4-(4-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine (7.99 g,18.23 mmol), Pd₂(dba)₃ (0.50 g, 0.55 mmol), P(t-Bu)₃ (0.22 g, 1.09mmol), NaOt-Bu (5.25 g, 54.68 mmol) according to the same way used for9-2 above.

FD-MS values for compounds 5-1 to 9-38 are given in Table 3 below.

TABLE 3 Compound FD-MS Compound FD-MS 5-1 m/z = 592.20 (C₄₂H₂₈N₂S =592.75) 5-2 m/z = 668.23 (C₄₈H₃₂N₂S = 668.85) 5-3 m/z = 642.21(C₄₆H₃₀N₂S = 642.81) 5-4 m/z = 642.21 (C₄₆H₃₀N₂S = 642.81) 5-5 m/z =744.26 (C₅₄H₃₆N₂S = 744.94) 5-6 m/z = 708.26 (C₅₁H₃₆N₂S = 708.91) 5-7m/z = 832.29 (C₆₁H₄₀N₂S = 833.05) 5-8 m/z = 692.23 (C₅₀H₃₂N₂S = 692.87)5-9 m/z = 692.23 (C₅₀H₃₂N₂S = 692.87) 5-10 m/z = 718.24 (C₅₂H₃₄N₂S =718.90) 5-11 m/z = 758.28 (C₅₅H₃₈N₂S = 758.97) 5-12 m/z = 882.31(C₆₅H₄₂N₂S = 883.11) 5-13 m/z = 668.23 (C₄₈H₃₂N₂S = 668.85) 5-14 m/z =718.24 (C₅₂H₃₄N₂S = 718.90) 5-15 m/z = 744.26 (C₅₄H₃₆N₂S = 744.94) 5-16m/z = 784.29 (C₅₇H₄₀N₂S = 785.01) 5-17 m/z = 592.20 (C₄₂H₂₈N₂S = 592.75)5-18 m/z = 642.21 (C₄₆H₃₀N₂S = 642.81) 5-19 m/z = 692.23 (C₅₀H₃₂N₂S =692.87) 5-20 m/z = 744.26 (C₅₄H₃₆N₂S = 744.94) 5-21 m/z = 668.23(C₄₈H₃₂N₂S = 668.85) 5-22 m/z = 718.24 (C₅₂H₃₄N₂S = 718.90) 5-23 m/z =784.29 (C₅₇H₄₀N₂S = 785.01) 5-24 m/z = 592.20 (C₄₂H₂₈N₂S = 592.75) 5-25m/z = 668.23 (C₄₈H₃₂N₂S = 668.85) 5-26 m/z = 642.21 (C₄₆H₃₀N₂S = 642.81)5-27 m/z = 642.21 (C₄₆H₃₀N₂S = 642.81) 5-28 m/z = 744.26 (C₅₄H₃₆N₂S =744.94) 5-29 m/z = 708.26 (C₅₁H₃₆N₂S = 708.91) 5-30 m/z = 832.29(C₆₁H₄₀N₂S = 833.05) 5-31 m/z = 692.23 (C₅₀H₃₂N₂S = 692.87) 5-32 m/z =692.23 (C₅₀H₃₂N₂S = 692.87) 5-33 m/z = 718.24 (C₅₂H₃₄N₂S = 718.90) 5-34m/z = 758.28 (C₅₅H₃₈N₂S = 758.97) 5-35 m/z = 882.31 (C₆₅H₄₂N₂S = 883.11)5-36 m/z = 668.23 (C₄₈H₃₂N₂S = 668.85) 5-37 m/z = 718.24 (C₅₂H₃₄N₂S =718.90) 5-38 m/z = 744.26 (C₅₄H₃₆N₂S = 744.94) 5-39 m/z = 784.29(C₅₇H₄₀N₂S = 785.01) 5-40 m/z = 592.20 (C₄₂H₂₈N₂S = 592.75) 5-41 m/z =642.21 (C₄₆H₃₀N₂S = 642.81) 5-42 m/z = 692.23 (C₅₀H₃₂N₂S = 692.87) 5-43m/z = 744.26 (C₅₄H₃₆N₂S = 744.94) 5-44 m/z = 668.23 (C₄₈H₃₂N₂S = 668.85)5-45 m/z = 718.24 (C₅₂H₃₄N₂S = 718.90) 5-46 m/z = 784.29 (C₅₇H₄₀N₂S =785.01) 5-47 m/z = 692.23 (C₅₀H₃₂N₂S = 692.87) 5-48 m/z = 718.24(C₅₂H₃₄N₂S = 718.90) 5-49 m/z = 794.28 (C₅₈H₃₈N₂S = 795.00) 5-50 m/z =682.24 (C₄₉H₃₄N₂S = 682.87) 5-51 m/z = 806.28 (C₅₉H₃₈N₂S = 807.01) 6-1m/z = 528.14 (C₃₅H₂₀N₄S = 528.63) 6-2 m/z = 533.17 (C₃₅H₁₅D₅N₄S =533.66) 6-3 m/z = 604.17 (C₄₁H₂₄N₄S = 604.72) 6-4 m/z = 604.17(C₄₁H₂₄N₄S = 604.72) 6-5 m/z = 578.16 (C₃₉H₂₂N₄S = 578.68) 6-6 m/z =578.16 (C₃₉H₂₂N₄S = 578.68) 6-7 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 6-8m/z = 644.20 (C₄₄H₂₈N₄S = 644.78) 6-9 m/z = 604.17 (C₄₁H₂₄N₄S = 604.72)6-10 m/z = 609.20 (C₄₁H₁₉D₅N₄S = 609.75) 6-11 m/z = 680.20 (C₄₇H₂₈N₄S =680.82) 6-12 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 6-13 m/z = 654.19(C₄₅H₂₆N₄S = 654.78) 6-14 m/z = 654.19 (C₄₅H₂₆N₄S = 654.78) 6-15 m/z =756.23 (C₅₃H₃₂N₄S = 756.91) 6-16 m/z = 720.23 (C₅₀H₃₂N₄S = 720.88) 6-17m/z = 604.17 (C₄₁H₂₄N₄S = 604.72) 6-18 m/z = 609.20 (C₄₁H₁₉D₅N₄S =609.75) 6-19 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 6-20 m/z = 680.20(C₄₇H₂₈N₄S = 680.82) 6-21 m/z = 654.19 (C₄₅H₂₆N₄S = 654.78) 6-22 m/z =654.19 (C₄₅H₂₆N₄S = 654.78) 6-23 m/z = 756.23 (C₅₃H₃₂N₄S = 756.91) 6-24m/z = 720.23 (C₅₀H₃₂N₄S = 720.88) 6-25 m/z = 528.14 (C₃₅H₂₀N₄S = 528.63)6-26 m/z = 533.17 (C₃₅H₁₅D₅N₄S = 533.66) 6-27 m/z = 604.17 (C₄₁H₂₄N₄S =604.72) 6-28 m/z = 604.17 (C₄₁H₂₄N₄S = 604.72) 6-29 m/z = 578.16(C₃₉H₂₂N₄S = 578.68) 6-30 m/z = 578.16 (C₃₉H₂₂N₄S = 578.68) 6-31 m/z =680.20 (C₄₇H₂₈N₄S = 680.82) 6-32 m/z = 644.20 (C₄₄H₂₈N₄S = 644.78) 6-33m/z = 604.17 (C₄₁H₂₄N₄S = 604.72) 6-34 m/z = 609.20 (C₄₁H₁₉D₅N₄S =609.75) 6-35 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 6-36 m/z = 680.20(C₄₇H₂₈N₄S = 680.82) 6-37 m/z = 654.19 (C₄₅H₂₆N₄S = 654.78) 6-38 m/z =654.19 (C₄₅H₂₆N₄S = 654.78) 6-39 m/z = 756.23 (C₅₃H₃₂N₄S = 756.91) 6-40m/z = 720.23 (C₅₀H₃₂N₄S = 720.88) 6-41 m/z = 604.17 (C₄₁H₂₄N₄S = 604.72)6-42 m/z = 609.20 (C₄₁H₁₉D₅N₄S = 609.75) 6-43 m/z = 680.20 (C₄₇H₂₈N₄S =680.82) 6-44 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 6-45 m/z = 654.19(C₄₅H₂₆N₄S = 654.78) 6-46 m/z = 654.19 (C₄₅H₂₆N₄S = 654.78) 6-47 m/z =756.23 (C₅₃H₃₂N₄S = 756.91) 6-48 m/z = 720.23 (C₅₀H₃₂N₄S = 720.88) 7-1m/z = 528.14 (C₃₅H₂₀N₄S = 528.63) 7-2 m/z = 533.17 (C₃₅H₁₅D₅N₄S =533.66) 7-3 m/z = 604.17 (C₄₁H₂₄N₄S = 604.72) 7-4 m/z = 604.17(C₄₁H₂₄N₄S = 604.72) 7-5 m/z = 578.16 (C₃₉H₂₂N₄S = 578.68) 7-6 m/z =578.16 (C₃₉H₂₂N₄S = 578.68) 7-7 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 7-8m/z = 644.20 (C₄₄H₂₈N₄S = 644.78) 7-9 m/z = 604.17 (C₄₁H₂₄N₄S = 604.72)7-10 m/z = 609.20 (C₄₁H₁₉D₅N₄S = 609.75) 7-11 m/z = 680.20 (C₄₇H₂₈N₄S =680.82) 7-12 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 7-13 m/z = 654.19(C₄₅H₂₆N₄S = 654.78) 7-14 m/z = 654.19 (C₄₅H₂₆N₄S = 654.78) 7-15 m/z =756.23 (C₅₃H₃₂N₄S = 756.91) 7-16 m/z = 720.23 (C₅₀H₃₂N₄S = 720.88) 7-17m/z = 604.17 (C₄₁H₂₄N₄S = 604.72) 7-18 m/z = 609.20 (C₄₁H₁₉D₅N₄S =609.75) 7-19 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 7-20 m/z = 680.20(C₄₇H₂₈N₄S = 680.82) 7-21 m/z = 654.19 (C₄₅H₂₆N₄S = 654.78) 7-22 m/z =654.19 (C₄₅H₂₆N₄S = 654.78) 7-23 m/z = 756.23 (C₅₃H₃₂N₄S = 756.91) 7-24m/z = 720.23 (C₅₀H₃₂N₄S = 720.88) 7-25 m/z = 528.14 (C₃₅H₂₀N₄S = 528.63)7-26 m/z = 533.17 (C₃₅H₁₅D₅N₄S = 533.66) 7-27 m/z = 604.17 (C₄₁H₂₄N₄S =604.72) 7-28 m/z = 604.17 (C₄₁H₂₄N₄S = 604.72) 7-29 m/z = 578.16(C₃₉H₂₂N₄S = 578.68) 7-30 m/z = 578.16 (C₃₉H₂₂N₄S = 578.68) 7-31 m/z =680.20 (C₄₇H₂₈N₄S = 680.82) 7-32 m/z = 644.20 (C₄₄H₂₈N₄S = 644.78) 7-33m/z = 604.17 (C₄₁H₂₄N₄S = 604.72) 7-34 m/z = 609.20 (C₄₁H₁₉D₅N₄S =609.75) 7-35 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 7-36 m/z = 680.20(C₄₇H₂₈N₄S = 680.82) 7-37 m/z = 654.19 (C₄₅H₂₆N₄S = 654.78) 7-38 m/z =654.19 (C₄₅H₂₆N₄S = 654.78) 7-39 m/z = 756.23 (C₅₃H₃₂N₄S = 756.91) 7-40m/z = 720.23 (C₅₀H₃₂N₄S = 720.88) 7-41 m/z = 604.17 (C₄₁H₂₄N₄S = 604.72)7-42 m/z = 609.20 (C₄₁H₁₉D₅N₄S = 609.75) 7-43 m/z = 680.20 (C₄₇H₂₈N₄S =680.82) 7-44 m/z = 680.20 (C₄₇H₂₈N₄S = 680.82) 7-45 m/z = 654.19(C₄₅H₂₆N₄S = 654.78) 7-46 m/z = 654.19 (C₄₅H₂₆N₄S = 654.78) 7-47 m/z =756.23 (C₅₃H₃₂N₄S = 756.91) 7-48 m/z = 720.23 (C₅₀H₃₂N₄S = 720.88) 8-1m/z = 603.18 (C₄₂H₂₅N₃S = 603.74) 8-2 m/z = 603.18 (C₄₂H₂₅N₃S = 603.74)8-3 m/z = 629.19 (C₄₄H₂₇N₃S = 629.78) 8-4 m/z = 629.19 (C₄₄H₂₇N₃S =629.78) 8-5 m/z = 679.21 (C₄₈H₂₉N₃S = 679.84) 8-6 m/z = 705.22(C₅₀H₃₁N₃S = 705.88) 8-7 m/z = 693.19 (C₄₈H₂₇N₃S = 693.82) 8-8 m/z =735.18 (C₅₀H₂₉N₃S₂ = 735.92) 8-9 m/z = 719.24 (C₅₁H₃₃N₃S = 719.91) 8-10m/z = 794.25 (C₅₆H₃₄N₃S = 794.98) 8-11 m/z = 705.22 (C₅₀H₃₁N₃S = 705.88)8-12 m/z = 639.26 (C₄₄H₁₇₁D₁₀N₃S = 639.84) 8-13 m/z = 685.26 (C₄₈H₃₅N₃S= 685.89) 8-14 m/z = 735.18 (C₅₀H₂₉N₃S₂ = 735.92) 8-15 m/z = 755.24(C₅₄H₃₃N₃S = 755.94) 8-16 m/z = 861.23 (C₆₀H₃₅N₃S₂ = 862.08) 8-17 m/z =785.20 (C₅₄H₃₁N₃S₂ = 785.98) 8-18 m/z = 753.24 (C₅₄H₃₁N₃O₂ = 753.86)8-19 m/z = 719.20 (C₅₀H₂₈N₃OS = 719.86) 8-20 m/z = 613.22 (C₄₄H₂₇N₃O =613.72) 8-21 m/z = 604.17 (C₄₁H₂₄N₄S = 604.73) 8-22 m/z = 604.17(C₄₁H₂₄N₄S = 604.73) 8-23 m/z = 630.19 (C₄₃H₂₆N₄S = 630.77) 8-24 m/z =630.19 (C₄₃H₂₆N₄S = 630.77) 8-25 m/z = 680.20 (C₄₇H₂₈N₄S = 680.83) 8-26m/z = 706.22 (C₄₉H₃₀N₄S = 706.87) 8-27 m/z = 694.18 (C₄₇H₂₆N₄OS =694.81) 8-28 m/z = 736.18 (C₄₉H₂₈N₄S₂ = 736.91) 8-29 m/z = 720.23(C₅₀H₃₂N₄S = 720.89) 8-30 m/z = 795.25 (C₅₅H₃₃N₅S = 795.96) 8-31 m/z =640.25 (C₄₃H₁₆D₁₀N₄S = 640.83) 8-32 m/z = 736.18 (C₄₉H₂₈N₄S₂ = 736.91)8-33 m/z = 756.23 (C₅₃H₃₂N₄S = 756.93) 8-34 m/z = 862.22 (C₅₉H₃₄N₄S₂ =863.07) 8-35 m/z = 796.23 (C₅₅H₃₂N₄OS = 796.95) 8-36 m/z = 905.32(C₆₅H₃₉N₅O = 906.06) 9-1 m/z = 603.18 (C₄₂H₂₅N₃S = 603.74) 9-2 m/z =603.18 (C₄₂H₂₅N₃S = 603.74) 9-3 m/z = 629.19 (C₄₄H₂₇N₃S = 629.78) 9-4m/z = 629.19 (C₄₄H₂₇N₃S = 629.78) 9-5 m/z = 679.21 (C₄₈H₂₉N₃S = 679.84)9-6 m/z = 705.22 (C₅₀H₃₁N₃S = 705.88) 9-7 m/z = 693.19 (C₄₈H₂₇N₃OS =693.82) 9-8 m/z = 735.18 (C₅₀H₂₉N₃S₂ = 735.92) 9-9 m/z = 719.24(C₅₁H₃₃N₃S = 719.91) 9-10 m/z = 794.25 (C₅₆H₃₄N₄S = 794.98) 9-11 m/z =705.22 (C₅₀H₃₁N₃S = 705.88) 9-12 m/z = 639.26 (C₄₄H₁₇D₁₀N₃S = 639.84)9-13 m/z = 685.26 (C₄₈H₃₅N₃S = 685.89) 9-14 m/z = 735.18 (C₅₀H₂₉N₃S₂ =735.92) 9-15 m/z = 755.24 (C₅₄H₃₃N₃S = 755.94) 9-16 m/z = 861.23(C₆₀H₃₅N₃S₂ = 862.08) 9-17 m/z = 785.20 (C₅₄H₃₁N₃S₂ = 785.98) 9-18 m/z =753.24 (C₅₄H₃₁N₃O₂ = 753.86) 9-19 m/z = 719.20 (C₅₀H₂₉N₃OS = 719.86)9-20 m/z = 613.22 (C₄₄H₂₇N₃O = 613.72) 9-21 m/z = 604.17 (C₄₁H₂₄N₄S =604.73) 9-22 m/z = 604.17 (C₄₁H₂₄N₄S = 604.73) 9-23 m/z = 630.19(C₄₃H₂₆N₄S = 630.77) 9-24 m/z = 630.19 (C₄₃H₂₆N₄S = 630.77) 9-25 m/z =680.20 (C₄₇H₂₈N₄S = 680.83) 9-26 m/z = 706.22 (C₄₉H₃₀N₄S = 706.87) 9-27m/z = 694.18 (C₄₇H₂₆N₄OS = 694.81) 9-28 m/z = 736.18 (C₄₉H₂₈N₄S₂ =736.91) 9-29 m/z = 720.23 (C₅₀H₃₂N₄S = 720.89) 9-30 m/z = 795.25(C₅₅H₃₃N₅S = 795.96) 9-31 m/z = 640.25 (C₄₃H₁₆D₁₀N₄S = 640.83) 9-32 m/z= 736.18 (C₄₉H₂₈N₄S₂ = 736.91) 9-33 m/z = 756.23 (C₅₃H₃₂N₄S = 756.93)9-34 m/z = 862.22 (C₅₉H₃₄N₄S₂ = 863.07) 9-35 m/z = 796.23 (C₅₅H₃₂N₄OS =796.95) 9-36 m/z = 905.32 (C₆₅H₃₉N₅O = 906.06) 9-37 m/z = 981.35(C₇₁H₄₃N₅O = 982.16) 9-38 m/z = 846.25 (C₅₉H₃₄N₄OS = 847.01)

Fabrication and Evaluation of Organic Electric Element Test Example 1(Phosphorescent Green Host)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using the synthesized inventive compounds as alight emitting host material of a light emitting layer. Each OLED wasfabricated as follows. First, an ITO layer (anode) was formed on a glasssubstrate, and a film ofN¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine (hereinafter abbreviated as “2-TNATA”) wasvacuum-deposited on the ITO layer to form a hole injection layer with athickness of 60 nm. Subsequently, a film of4,4-bis[N-(1-naphthyl)-N-phenyl amino]biphenyl (hereinafter abbreviatedas “NPD”) was vacuum-deposited with a thickness of 20 nm on the holeinjection layer to form a hole transport layer. Also, a light emittinglayer with a thickness of30 nm was deposited on the hole transport layerby doping the hole transport layer with the inventive compound(1-1-1-32, 2-1-2-32, 3-1-3-27, 4-1-4-27) as a host material and[tris(2-phenylpyridine)-iridium](hereinafter abbreviated as “Ir(ppy)₃”)as a dopant material in a weight ratio of 95:5. Next, a film of(1,1′-bisphenyl)-4-olato) bis(2-methyl-8-quinolinolato)aluminum(hereinafter abbreviated as “BAlq”) was vacuum-deposited with athickness of 10 nm on the light emitting layer to form a hole blockinglayer, and then a film of tris(8-quinolinolato)aluminum (hereinafterabbreviated as “Alq₃”) was formed with a thickness of 40 nm on the holeblocking layer to form an electron injection layer. Next, LiF ashalogenated alkali metal was deposited with a thickness of 0.2 nm on theelectron injection layer, and then Al was deposited with a thickness of150 nm thereon to form an Al/LiF cathode. In this way, an OLED wascompleted.

Comparative Example 1

An OLED was manufactured in the same manner as described in Test Example1, except that Comparative Compound 1(4,4′-di(9H-carbazol-9-yl)-1,1′-biphenyl) represented below was used asthe host material of the light emitting layer, instead of the inventivecompound.

Comparative Example 2

An OLED was manufactured in the same manner as described in Test Example1, except that Comparative Compound 2(9-(9-(4,6-diphenylpyrimidin-2-yl)-9H-carbazol-3-yl)-12-phenyl-12H-benzo[4,5]thieno[3,2-a]carbazole)represented below was used as the host material of the light emittinglayer, instead of the inventive compound.

Comparative Example 3

An OLED was manufactured in the same manner as described in Test Example1, except that Comparative Compound 3(3-(9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazol-3-yl)-12-phenyl-12H-benzo[4,5]thieno[2,3-a]carbazole)represented below was used as the host material of the light emittinglayer, instead of the inventive compound.

Comparative Example 4

An OLED was manufactured in the same manner as described in Test Example1, except that Comparative Compound 4(12-(5-phenylpyrimidin-2-yl)-12H-benzo[4,5]thieno[3,2-a]carbazole)represented below was used as the host material of the light emittinglayer, instead of the inventive compound.

Comparative Example 5

An OLED was manufactured in the same manner as described in Test Example1, except that Comparative Compound 5(12-(4-(4,6-diphenylpyrimidin-2-yl)phenyl)-12H-benzo[4,5]thieno[2,3-a]carbazole)represented below was used as the host material of the light emittinglayer, instead of the inventive compound.

A forward bias DC voltage was applied to each of the OLEDs manufacturedin Test Example 1 and Comparative Examples 1 to 5, andelectro-luminescence (EL) characteristics of the OLED were measured byPR-650 (Photoresearch). Also, T95 life span was measured by life spanmeasuring equipment (Mc science) at a reference brightness of 300 cd/m².Table 4 below shows the measurement results. In Table 4, Examples 1 to103 represent the inventive OLEDs manufactured according to Test Example1.

TABLE 4 Current Driving Density Brightness Efficiency CIE CompondVoltage (mA/cm2) (cd/m2) (cd/A) T(95) (x, y) Comp. Ex. (1) Comp. Com.(1) 6.3 7.0 300 4.3 51.8 (0.33, 0.61) Comp. Ex. (2) Comp. Com. (2) 5.85.9 300 5.1 70.6 (0.33, 0.61) Comp. Ex. (3) Comp. Com. (3) 5.7 6.0 300 565.6 (0.33, 0.61) Comp. Ex. (4) Comp. Com. (4) 5.6 5.8 300 5.2 82.5(0.33, 0.61) Comp. Ex. (5) Comp. Com. (5) 5.6 5.9 300 5.1 86.7 (0.33,0.61) Ex. (1) Com. (1-1) 5.3 4.6 300 6.6 110.6 (0.32, 0.61) Ex. (2) Com.(1-2) 5.1 4.7 300 6.4 113.9 (0.33, 0.60) Ex. (3) Com. (1-3) 5.1 4.9 3006.2 109.0 (0.30, 0.61) Ex. (4) Com. (1-4) 5.4 5.0 300 6.0 107.5 (0.300.61) Ex. (5) Com. (1-5) 5.4 4.6 300 6.6 108.9 (0.31, 0.60) Ex. (6) Com.(1-6) 5.6 5.8 300 5.2 82.7 (0.33, 0.61) Ex. (7) Com. (1-7) 5.0 5.0 3006.0 115.7 (0.32, 0.60) Ex. (8) Com. (1-8) 4.9 4.3 300 7.0 136.2 (0.32,0.61) Ex. (9) Com. (1-9) 5.0 4.2 300 7.2 145.9 (0.33, 0.60) Ex. (10)Com. (1-10) 5.3 4.7 300 6.3 137.4 (0.30, 0.60) Ex. (11) Com. (1-11) 5.24.3 300 7.0 145.2 (0.30, 0.61) Ex. (12) Com. (1-12) 4.9 4.7 300 6.4134.8 (0.31, 0.61) Ex. (13) Com. (1-13) 5.5 5.7 300 5.3 93.5 (0.31,0.61) Ex. (14) Com. (1-14) 4.9 5.1 300 5.9 130.8 (0.31, 0.60) Ex. (15)Com. (1-15) 5.2 4.5 300 6.7 132.9 (0.31, 0.60) Ex. (16) Com. (1-16) 5.15.2 300 5.8 114.5 (0.32, 0.61) Ex. (17) Com. (1-17) 5.0 4.0 300 7.5147.7 (0.31, 0.61) Ex. (18) Com. (1-18) 5.0 4.2 300 7.2 137.7 (0.33,0.60) Ex. (19) Com. (1-19) 5.0 4.4 300 6.9 123.8 (0.31, 0.60) Ex. (20)Com. (1-20) 5.0 4.0 300 7.4 138.6 (0.32, 0.61) Ex. (21) Com. (1-21) 5.44.8 300 6.3 129.8 (0.32, 0.61) Ex. (22) Com. (1-22) 4.9 4.6 300 6.5132.2 (0.33, 0.60) Ex. (23) Com. (1-23) 5.0 4.9 300 6.2 115.0 (0.30,0.61) Ex. (24) Com. (1-24) 5.1 4.1 300 7.3 112.9 (0.31, 0.61) Ex. (25)Com. (1-25) 5.3 4.2 300 7.2 120.7 (0.30, 0.60) Ex. (26) Com. (1-26) 4.95.2 300 5.8 120.6 (0.33, 0.61) Ex. (27) Com. (1-27) 5.3 4.4 300 6.9140.7 (0.32, 0.61) Ex. (28) Com. (1-28) 5.0 4.2 300 7.2 137.7 (0.33,0.60) Ex. (29) Com. (1-29) 5.3 5.1 300 5.9 106.8 (0.30, 0.61) Ex. (30)Com. (1-30) 5.1 4.6 300 6.6 139.2 (0.31, 0.61) Ex. (31) Com. (1-31) 5.04.8 300 6.3 143.0 (0.31, 0.60) Ex. (32) Com. (1-32) 5.2 4.2 300 7.2123.3 (0.33, 0.61) Ex. (33) Com. (2-1) 4.9 5.2 300 5.8 149.0 (0.32,0.60) Ex. (34) Com. (2-2) 5.4 5.3 300 5.6 123.5 (0.32, 0.61) Ex. (35)Com. (2-3) 5.2 4.7 300 6.3 129.4 (0.33, 0.60) Ex. (36) Com. (2-4) 5.05.2 300 5.8 105.8 (0.30, 0.60) Ex. (37) Com. (2-5) 5.0 4.9 300 6.1 132.9(0.30, 0.61) Ex. (38) Com. (2-6) 5.6 6.1 300 4.9 80.2 (0.32, 0.61) Ex.(39) Com. (2-7) 5.1 4.5 300 6.7 131.2 (0.30, 0.61) Ex. (40) Com. (2-8)5.1 4.8 300 6.3 117.8 (0.31, 0.60) Ex. (41) Com. (2-9) 5.3 5.1 300 5.9102.8 (0.31, 0.60) Ex. (42) Com. (2-10) 5.0 4.2 300 7.2 108.6 (0.32,0.61) Ex. (43) Com. (2-11) 5.1 4.7 300 6.3 114.6 (0.31, 0.61) Ex. (44)Com. (2-12) 5.0 5.2 300 5.8 114.4 (0.33, 0.60) Ex. (45) Com. (2-13) 5.75.8 300 5.2 81.9 (0.31, 0.60) Ex. (46) Com. (2-14) 4.9 5.1 300 5.8 131.1(0.32, 0.60) Ex. (47) Com. (2-15) 4.8 4.9 300 6.1 119.0 (0.32, 0.61) Ex.(48) Com. (2-16) 4.9 4.6 300 6.6 139.4 (0.33, 0.60) Ex. (49) Com. (2-17)4.9 5.3 300 5.6 131.2 (0.30, 0.61) Ex. (50) Com. (2-18) 5.3 4.7 300 6.4136.8 (0.31, 0.61) Ex. (51) Com. (2-19) 5.0 4.4 300 6.8 127.5 (0.31,0.60) Ex. (52) Com. (2-20) 5.0 4.3 300 7.0 145.6 (0.33, 0.61) Ex. (53)Com.(2-21) 5.1 5.0 300 6.0 132.6 (0.32, 0.61) Ex. (54) Com. (2-22) 4.95.1 300 5.9 106.9 (0.33, 0.60) Ex. (55) Com. (2-23) 5.3 4.5 300 6.7127.7 (0.30, 0.61) Ex. (56) Com. (2-24) 4.9 4.5 300 6.7 110.6 (0.31,0.61) Ex. (57) Com. (2-25) 5.3 4.4 300 6.8 116.4 (0.31, 0.60) Ex. (58)Com. (2-26) 5.0 4.5 300 6.7 102.7 (0.33, 0.61) Ex. (59) Com. (2-27) 5.34.2 300 7.1 105.1 (0.32, 0.60) Ex. (60) Com. (2-28) 4.9 4.0 300 7.5100.7 (0.32, 0.60) Ex. (61) Com. (2-29) 5.3 5.3 300 5.6 137.9 (0.33,0.60) Ex. (62) Com. (2-30) 5.1 4.1 300 7.2 123.7 (0.30, 0.60) Ex. (63)Com. (2-31) 5.3 4.8 300 6.2 123.7 (0.30, 0.61) Ex. (64) Com. (2-32) 5.04.4 300 6.9 112.8 (0.32, 0.60) Ex. (65) Com. (3-1) 5.2 4.2 300 7.1 103.2(0.31, 0.61) Ex. (66) Com. (3-2) 5.2 4.7 300 6.4 135.2 (0.31, 0.60) Ex.(67) Com. (3-3) 4.8 4.5 300 6.6 140.5 (0.31, 0.60) Ex. (68) Com. (3-4)5.0 4.2 300 7.1 141.5 (0.32, 0.61) Ex. (69) Com. (3-5) 4.8 4.7 300 6.3133.8 (0.31, 0.61) Ex. (70) Com. (3-6) 5.6 5.8 300 5.2 93.1 (0.33, 0.60)Ex. (71) Com. (3-7) 5.0 4.0 300 7.5 112.9 (0.31, 0.60) Ex. (72) Com.(3-8) 5.3 4.9 300 6.1 130.1 (0.32, 0.61) Ex. (73) Com. (3-9) 5.1 4.2 3007.2 123.3 (0.32, 0.61) Ex. (74) Com. (3-10) 4.8 4.5 300 6.6 149.0 (0.33,0.60) Ex. (75) Com. (3-11) 5.1 4.6 300 6.5 106.1 (0.30, 0.61) Ex. (76)Com. (3-12) 5.0 4.3 300 7.0 127.6 (0.31, 0.61) Ex. (77) Com. (3-13) 5.55.8 300 5.2 85.6 (0.31, 0.60) Ex. (78) Com. (3-14) 5.1 4.9 300 6.2 134.0(0.33, 0.61) Ex. (79) Com. (3-15) 5.2 4.5 300 6.7 132.2 (0.32, 0.61) Ex.(80) Com. (3-16) 5.3 4.7 300 6.4 124.4 (0.33, 0.60) Ex. (81) Com. (3-17)5.1 4.3 300 7.0 113.8 (0.32, 0.61) Ex. (82) Com. (3-18) 5.0 4.1 300 7.3147.6 (0.33, 0.60) Ex. (83) Com. (3-19) 5.1 4.2 300 7.1 100.6 (0.30,0.61) Ex. (84) Com. (3-20) 4.9 5.0 300 6.0 106.7 (0.30, 0.61) Ex. (85)Com. (3-21) 5.0 5.1 300 5.9 140.2 (0.31, 0.60) Ex. (86) Com. (3-22) 5.14.8 300 6.2 118.8 (0.33, 0.61) Ex. (87) Com. (3-23) 5.4 4.1 300 7.3100.0 (0.32, 0.60) Ex. (88) Com. (3-24) 5.2 5.0 300 6.0 121.2 (0.32,0.61) Ex. (89) Com. (3-25) 5.1 4.7 300 6.3 145.9 (0.33, 0.60) Ex. (90)Com. (3-26) 5.0 4.2 300 7.1 136.9 (0.30, 0.60) Ex. (91) Com. (3-27) 5.14.1 300 7.3 132.8 (0.30, 0.61) Ex. (92) Com. (4-1) 4.8 4.7 300 6.4 106.2(0.31, 0.61) Ex. (93) Com. (4-2) 5.3 5.1 300 5.9 106.6 (0.31, 0.61) Ex.(94) Com. (4-3) 4.9 4.3 300 7.0 146.7 (0.31, 0.60) Ex. (95) Com. (4-4)5.1 4.1 300 7.4 146.4 (0.31, 0.60) Ex. (96) Com. (4-5) 4.9 4.9 300 6.1135.8 (0.32, 0.61) Ex. (97) Com. (4-6) 5.7 6.0 300 5.0 80.3 (0.31, 0.61)Ex. (98) Com. (4-7) 4.8 4.4 300 6.8 127.4 (0.33, 0.60) Ex. (99) Com.(4-8) 5.3 4.9 300 6.1 131.6 (0.31, 0.60) Ex. (100) Com. (4-9) 4.9 5.1300 5.8 100.8 (0.32, 0.61) Ex. (101) Com. (4-10) 4.9 5.0 300 6.1 107.3(0.32, 0.61) Ex. (102) Com. (4-11) 5.2 4.6 300 6.5 119.6 (0.33, 0.60)Ex. (103) Com. (4-12) 4.9 4.2 300 7.2 127.7 (0.30, 0.61) Ex. (104) Com.(4-13) 5.6 5.8 300 5.2 84.7 (0.31, 0.61) Ex. (105) Com. (4-14) 5.0 4.7300 6.4 135.5 (0.30, 0.60) Ex. (106) Com. (4-15) 5.4 4.4 300 6.8 112.7(0.33, 0.61) Ex. (107) Com. (4-16) 5.1 4.0 300 7.4 107.2 (0.32, 0.61)Ex. (108) Com. (4-17) 5.1 4.4 300 6.7 139.7 (0.33, 0.60) Ex. (109) Com.(4-18) 5.2 5.1 300 5.9 104.8 (0.30, 0.61) Ex. (110) Com. (4-19) 5.1 4.6300 6.5 109.3 (0.31, 0.61) Ex. (111) Com. (4-20) 4.9 4.6 300 6.5 115.0(0.31, 0.60) Ex. (112) Com. (4-21) 5.3 5.2 300 5.8 139.2 (0.33, 0.61)Ex. (113) Com. (4-22) 5.2 5.0 300 5.9 133.3 (0.32, 0.60) Ex. (114) Com.(4-23) 4.9 4.1 300 7.2 141.0 (0.32, 0.61) Ex. (115) Com. (4-24) 5.3 5.3300 5.7 137.9 (0.33, 0.60) Ex. (116) Com. (4-25) 5.3 4.3 300 7.0 120.8(0.30, 0.60) Ex. (117) Com. (4-26) 5.2 5.1 300 5.9 124.0 (0.30, 0.61)Ex. (118) Com. (4-27) 4.9 4.4 300 6.8 107.0 (0.32, 0.61)

It can be seen from the results given in Table 4 above that most of theOLEDs manufactured using the inventive compounds showed low drivingvoltage, high efficiency, and long life span, as compared to ComparativeExamples 1 to 5. Also, the inventive compounds, each containingheterocyclic groups at positions R₁ to R₄ and R₁₁ to R₁₄ of the core,showed relatively high driving voltage, low efficiency, and short lifespan as in the case of Comparative Examples 2 and 3. This is believedbecause when heterocyclic groups are linked to positions R₁ to R₄ andR₁₁ to R₁₄, the band gap is relatively low, HOMO is increased, holemobility is reduced, and driving voltage is increased, resulting in lowefficiency and short lifespan. It can also be noted that ComparativeExamples 4 and 5, which are compounds substituted by hydrogen atpositions R₁ to R₄ and R₁₁ to R₁₄, showed shorter life span than theinventive compounds.

Test Example 2 (Phosphorescent Red Host)

First, an ITO layer (anode) was formed on a glass substrate, and 2-TNATAwas vacuum-deposited on the ITO layer to form a hole injection layerwith a thickness of 60 nm. Subsequently, NPD was vacuum-deposited with athickness of 20 nm on the hole injection layer to form a hole transportlayer. Next, a light emitting layer with a thickness of 30 nm wasdeposited on the hole transport layer by doping the hole transport layerwith the inventive compound (3-28-3-51, 4-28-4-51, 6-1-6-48, 7-1-7-48)as a host material and(piq)2Ir(acac)[bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] asa dopant material in a weight ratio of 95:5. Also, BAlq wasvacuum-deposited with a thickness of 10 nm on the light emitting layerto form a hole blocking layer, and a film of Alq₃ was formed with athickness of 40 nm on the hole blocking layer to form an electroninjection layer.

Next, LiF as halogenated alkali metal was deposited with a thickness of0.2 nm on the electron injection layer, and then Al was deposited with athickness of 150 nm thereon to form an Al/LiF cathode. In this way, anOLED was completed.

Comparative Example 6

An OLED was manufactured in the same manner as described in Test Example2, except that Comparative Compound 1(4,4′-di(9H-carbazol-9-yl)-1,1′-biphenyl) was used as the host materialof the light emitting layer, instead of the inventive compound.

Comparative Example 7

An OLED was manufactured in the same manner as described in Test Example2, except that Comparative Compound 2(9-(9-(4,6-diphenylpyrimidin-2-yl)-9H-carbazol-3-yl)-12-phenyl-12H-benzo[4,5]thieno[3,2-a]carbazole)was used as the host material of the light emitting layer, instead ofthe inventive compound.

Comparative Example 8

An OLED was manufactured in the same manner as described in Test Example2, except that Comparative Compound 3(3-(9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazol-3-yl)-12-phenyl-12H-benzo[4,5]thieno[2,3-a]carbazole)was used as the host material of the light emitting layer, instead ofthe inventive compound.

Comparative Example 9

An OLED was manufactured in the same manner as described in Test Example2, except that Comparative Compound 4(12-(5-phenylpyrimidin-2-yl)-12H-benzo[4,5]thieno[3,2-a]carbazole) wasused as the host material of the light emitting layer, instead of theinventive compound.

Comparative Example 10

An OLED was manufactured in the same manner as described in Test Example2, except that Comparative Compound 5(12-(4-(4,6-diphenylpyrimidin-2-yl)phenyl)-12H-benzo[4,5]thieno[2,3-a]carbazole)was used as the host material of the light emitting layer, instead ofthe inventive compound.

A forward bias DC voltage was applied to each of the OLEDs manufacturedin Test Example 2 and Comparative Examples 6 to 10, and ELcharacteristics of the OLED were measured by PR-650 (Photo research).Also, T95 life span was measured by life span measuring equipment (Mcscience) at a reference brightness of 300 cd/m². Table 5 below shows themeasurement results. In Table 5, Examples 119 to 262 represent theinventive OLEDs manufactured according to Test Example 2.

TABLE 5 Current Driving Density Brightness Efficiency CIE CompondVoltage (mA/cm2) (cd/m2) (cd/A) T(95) (x, y) Comp. Ex. (6) Comp. Com.(1) 6.0 7.5 300 4.0 55.6 (0.62, 0.37) Comp. Ex. (7) Comp. Com. (2) 5.45.6 300 5.4 76.4 (0.62, 0.37) Comp. Ex. (8) Comp. Com. (3) 5.6 5.2 3005.8 86.8 (0.62, 0.37) Comp. Ex. (9) Comp. Com. (4) 5.5 5.8 300 5.2 72.9(0.62, 0.37) Comp. Ex. (10) Comp. Com. (5) 5.7 6.3 300 4.8 71.7 (0.62,0.37) Ex. (119) Com. (3-28) 5.2 4.9 300 6.2 131.0 (0.66, 0.32) Ex. (120)Com. (3-29) 5.3 4.8 300 6.2 129.0 (0.67, 0.33) Ex. (121) Com. (3-30) 5.24.8 300 6.2 97.4 (0.67, 0.33) Ex. (122) Com. (3-31) 4.9 4.6 300 6.5122.2 (0.65, 0.33) Ex. (123) Com. (3-32) 5.0 4.2 300 7.2 138.5 (0.67,0.32) Ex. (124) Com. (3-33) 5.1 4.8 300 6.2 115.4 (0.66, 0.32) Ex. (125)Com. (3-34) 5.3 4.0 300 7.5 129.3 (0.66, 0.33) Ex. (126) Com. (3-35) 4.84.1 300 7.4 136.9 (0.66, 0.33) Ex. (127) Com. (3-36) 5.3 4.4 300 6.9125.7 (0.66, 0.32) Ex. (128) Com. (3-37) 5.3 4.8 300 6.2 110.5 (0.66,0.32) Ex. (129) Com. (3-38) 5.1 4.2 300 7.1 126.3 (0.66, 0.32) Ex. (130)Com. (3-39) 4.8 5.1 300 5.9 96.0 (0.66, 0.33) Ex. (131) Com. (3-40) 5.04.6 300 6.5 121.8 (0.67, 0.32) Ex. (132) Com. (3-41) 5.3 4.6 300 6.5122.6 (0.66, 0.33) Ex. (133) Com. (3-42) 4.9 4.4 300 6.9 130.4 (0.65,0.32) Ex. (134) Com. (3-43) 4.9 4.7 300 6.3 135.9 (0.66, 0.32) Ex. (135)Com. (3-44) 5.2 4.2 300 7.2 132.7 (0.66, 0.32) Ex. (136) Com. (3-45) 4.84.3 300 6.9 95.1 (0.66, 0.32) Ex. (137) Com. (3-46) 5.3 4.9 300 6.1125.3 (0.65, 0.33) Ex. (138) Com. (3-47) 5.2 4.5 300 6.6 101.7 (0.65,0.32) Ex. (139) Com. (3-48) 5.0 4.7 300 6.4 119.8 (0.67, 0.33) Ex. (140)Com. (3-49) 5.3 4.2 300 7.1 122.2 (0.66, 0.32) Ex. (141) Com. (3-50) 4.94.9 300 6.1 139.7 (0.67, 0.33) Ex. (142) Com. (3-51) 5.1 4.6 300 6.5105.8 (0.66, 0.33) Ex. (143) Com. (4-28) 5.3 4.3 300 6.9 122.1 (0.65,0.32) Ex. (144) Com. (4-29) 5.3 4.3 300 7.0 111.7 (0.66, 0.32) Ex. (145)Com. (4-30) 4.9 4.0 300 7.4 114.3 (0.67, 0.32) Ex. (146) Com. (4-31) 5.24.6 300 6.5 136.9 (0.65, 0.32) Ex. (147) Com. (4-32) 5.3 4.1 300 7.2131.4 (0.65, 0.33) Ex. (148) Com. (4-33) 4.9 4.3 300 7.0 137.5 (0.66,0.32) Ex. (149) Com. (4-34) 5.3 4.4 300 6.8 138.4 (0.67, 0.33) Ex. (150)Com. (4-35) 5.4 4.7 300 6.4 98.9 (0.66, 0.33) Ex. (151) Com. (4-36) 4.95.0 300 6.0 103.6 (0.66, 0.32) Ex. (152) Com. (4-37) 5.2 4.5 300 6.7131.1 (0.66, 0.33) Ex. (153) Com. (4-38) 5.1 4.8 300 6.3 127.2 (0.66,0.32) Ex. (154) Com. (4-39) 5.2 4.4 300 6.8 117.6 (0.65, 0.32) Ex. (155)Com. (4-40) 5.2 5.0 300 6.0 123.5 (0.65, 0.33) Ex. (156) Com. (4-41) 5.34.1 300 7.3 109.0 (0.66, 0.33) Ex. (157) Com. (4-42) 5.2 4.0 300 7.5106.0 (0.66, 0.33) Ex. (158) Com. (4-43) 5.0 4.5 300 6.6 119.5 (0.65,0.32) Ex. (159) Com. (4-44) 5.1 5.1 300 5.9 138.1 (0.66, 0.32) Ex. (160)Com. (4-45) 5.3 4.3 300 6.9 101.8 (0.66, 0.32) Ex. (161) Com. (4-46) 5.34.2 300 7.2 117.2 (0.67, 0.32) Ex. (162) Com. (4-47) 5.3 4.7 300 6.4100.5 (0.67, 0.33) Ex. (163) Com. (4-48) 5.2 4.4 300 6.8 105.5 (0.66,0.32) Ex. (164) Com. (4-49) 5.2 4.8 300 6.3 114.5 (0.65, 0.33) Ex. (165)Com. (4-50) 5.0 5.1 300 5.9 115.5 (0.67, 0.32) Ex. (166) Com. (4-51) 4.94.8 300 6.3 117.3 (0.66, 0.33) Ex. (167) Com. (6-1) 5.1 4.7 300.0 6.4131.4 (0.66, 0.32) Ex. (168) Com. (6-2) 5.1 4.1 300.0 7.4 128.3 (0.65,0.33) Ex. (169) Com. (6-3) 5.2 4.0 300.0 7.5 110.2 (0.65, 0.32) Ex.(170) Com. (6-4) 4.9 4.3 300.0 7.0 116.3 (0.67, 0.33) Ex. (171) Com.(6-5) 4.9 4.3 300.0 7.0 97.3 (0.66, 0.32) Ex. (172) Com. (6-6) 5.2 4.2300.0 7.1 105.6 (0.67, 0.33) Ex. (173) Com. (6-7) 4.9 4.2 300.0 7.2126.2 (0.66, 0.33) Ex. (174) Com. (6-8) 5.1 4.1 300.0 7.3 118.4 (0.65,0.32) Ex. (175) Com. (6-9) 5.3 4.8 300.0 6.3 108.1 (0.66, 0.32) Ex.(176) Com. (6-10) 5.2 4.3 300.0 7.0 127.3 (0.67, 0.32) Ex. (177) Com.(6-11) 4.8 4.3 300.0 7.0 134.8 (0.65, 0.32) Ex. (178) Com. (6-12) 4.94.5 300.0 6.7 139.0 (0.65, 0.33) Ex. (179) Com. (6-13) 5.0 4.3 300.0 7.0102.4 (0.66, 0.32) Ex. (180) Com. (6-14) 5.0 4.7 300.0 6.4 132.9 (0.67,0.33) Ex. (181) Com. (6-15) 5.0 4.2 300.0 7.2 104.3 (0.66, 0.33) Ex.(182) Com. (6-16) 5.0 4.4 300.0 6.8 126.0 (0.66, 0.32) Ex. (183) Com.(6-17) 4.8 4.4 300.0 6.8 133.7 (0.66, 0.33) Ex. (184) Com. (6-18) 5.14.7 300.0 6.4 121.3 (0.66, 0.32) Ex. (185) Com. (6-19) 4.9 4.0 300.0 7.4102.1 (0.65, 0.32) Ex. (186) Com. (6-20) 4.9 4.0 300.0 7.5 96.8 (0.65,0.33) Ex. (187) Com. (6-21) 5.2 4.1 300.0 7.4 117.6 (0.66, 0.32) Ex.(188) Com. (6-22) 5.1 4.1 300.0 7.3 96.9 (0.65, 0.33) Ex. (189) Com.(6-23) 4.9 4.5 300.0 6.7 106.8 (0.65, 0.32) Ex. (190) Com. (6-24) 5.14.1 300.0 7.3 136.7 (0.67, 0.33) Ex. (191) Com. (6-25) 4.9 4.1 300.0 7.397.2 (0.66, 0.32) Ex. (192) Com. (6-26) 5.2 4.1 300.0 7.4 112.6 (0.67,0.33) Ex. (193) Com. (6-27) 4.9 4.6 300.0 6.5 124.0 (0.66, 0.33) Ex.(194) Com. (6-28) 5.1 4.2 300.0 7.1 127.3 (0.65, 0.32) Ex. (195) Com.(6-29) 4.9 4.6 300.0 6.5 102.5 (0.66, 0.32) Ex. (196) Com. (6-30) 5.04.6 300.0 6.5 115.8 (0.67, 0.32) Ex. (197) Com. (6-31) 4.9 4.2 300.0 7.2138.2 (0.65, 0.32) Ex. (198) Com. (6-32) 4.9 4.4 300.0 6.8 134.9 (0.65,0.33) Ex. (199) Com. (6-33) 4.9 4.5 300.0 6.7 115.9 (0.66, 0.32) Ex.(200) Com. (6-34) 5.1 4.3 300.0 7.0 128.8 (0.67, 0.33) Ex. (201) Com.(6-35) 5.0 4.4 300.0 6.8 117.4 (0.66, 0.33) Ex. (202) Com. (6-36) 5.14.7 300.0 6.4 135.0 (0.66, 0.32) Ex. (203) Com. (6-37) 5.1 4.1 300.0 7.2124.0 (0.66, 0.33) Ex. (204) Com. (6-38) 5.1 4.7 300.0 6.4 105.6 (0.66,0.32) Ex. (205) Com. (6-39) 5.0 4.8 300.0 6.3 133.9 (0.65, 0.32) Ex.(206) Com. (6-40) 5.3 4.4 300.0 6.8 109.1 (0.65, 0.33) Ex. (207) Com.(6-41) 4.9 4.2 300.0 7.2 95.5 (0.66, 0.32) Ex. (208) Com. (6-42) 5.3 4.7300.0 6.4 109.6 (0.65, 0.33) Ex. (209) Com. (6-43) 5.1 4.7 300.0 6.3109.7 (0.65, 0.32) Ex. (210) Com. (6-44) 5.0 4.3 300.0 7.0 135.5 (0.67,0.33) Ex. (211) Com. (6-45) 5.2 4.8 300.0 6.3 131.0 (0.66, 0.32) Ex.(212) Com. (6-46) 4.9 4.2 300.0 7.2 109.1 (0.67, 0.33) Ex. (213) Com.(6-47) 4.8 4.1 300.0 7.2 108.6 (0.66, 0.33) Ex. (214) Com. (6-48) 5.04.5 300.0 6.7 116.7 (0.65, 0.32) Ex. (215) Com. (7-1) 5.2 4.6 300.0 6.5130.8 (0.66, 0.32) Ex. (216) Com. (7-2) 5.1 4.5 300.0 6.7 137.3 (0.67,0.32) Ex. (217) Com. (7-3) 5.1 4.5 300.0 6.6 123.2 (0.65, 0.32) Ex.(218) Com. (7-4) 5.2 4.6 300.0 6.5 101.9 (0.65, 0.33) Ex. (219) Com.(7-5) 5.1 4.4 300.0 6.8 119.1 (0.66, 0.32) Ex. (220) Com. (7-6) 5.0 4.5300.0 6.7 107.7 (0.67, 0.33) Ex. (221) Com. (7-7) 4.8 4.7 300.0 6.4128.5 (0.66, 0.33) Ex. (222) Com. (7-8) 4.9 4.2 300.0 7.1 101.7 (0.66,0.32) Ex. (223) Com. (7-9) 5.0 4.5 300.0 6.7 102.9 (0.66, 0.33) Ex.(224) Com. (7-10) 5.1 4.3 300.0 7.0 110.8 (0.66, 0.32) Ex. (225) Com.(7-11) 5.1 4.7 300.0 6.4 114.7 (0.65, 0.32) Ex. (226) Com. (7-12) 5.04.3 300.0 7.0 121.7 (0.65, 0.33) Ex. (227) Com. (7-13) 5.1 4.4 300.0 6.8121.2 (0.66, 0.32) Ex. (228) Com. (7-14) 5.0 4.4 300.0 6.9 128.8 (0.65,0.33) Ex. (229) Com. (7-15) 5.0 4.8 300.0 6.3 122.2 (0.65, 0.32) Ex.(230) Com. (7-16) 4.9 4.7 300.0 6.3 132.4 (0.67, 0.33) Ex. (231) Com.(7-17) 4.9 4.2 300.0 7.1 114.6 (0.66, 0.32) Ex. (232) Com. (7-18) 4.84.2 300.0 7.1 102.1 (0.67, 0.33) Ex. (233) Com. (7-19) 4.9 4.8 300.0 6.3135.9 (0.66, 0.33) Ex. (234) Com. (7-20) 5.1 4.2 300.0 7.1 113.2 (0.65,0.32) Ex. (235) Com. (7-21) 5.1 4.8 300.0 6.2 136.6 (0.66, 0.32) Ex.(236) Com. (7-22) 4.8 4.8 300.0 6.3 136.0 (0.67, 0.32) Ex. (237) Com.(7-23) 4.8 4.0 300.0 7.5 117.6 (0.65, 0.32) Ex. (238) Com. (7-24) 5.34.5 300.0 6.6 118.2 (0.65, 0.33) Ex. (239) Com. (7-25) 5.2 4.1 300.0 7.496.5 (0.66, 0.32) Ex. (240) Com. (7-26) 5.0 4.6 300.0 6.5 122.8 (0.67,0.33) Ex. (241) Com. (7-27) 4.8 4.6 300.0 6.6 138.3 (0.66, 0.33) Ex.(242) Com. (7-28) 4.9 4.7 300.0 6.3 127.8 (0.66, 0.32) Ex. (243) Com.(7-29) 5.3 4.2 300.0 7.2 116.1 (0.66, 0.33) Ex. (244) Com. (7-30) 4.94.1 300.0 7.3 117.2 (0.66, 0.32) Ex. (245) Com. (7-31) 4.9 4.3 300.0 6.9121.4 (0.65, 0.32) Ex. (246) Com. (7-32) 4.9 4.5 300.0 6.7 108.3 (0.65,0.33) Ex. (247) Com. (7-33) 5.1 4.4 300.0 6.9 123.9 (0.66, 0.32) Ex.(248) Com. (7-34) 5.1 4.2 300.0 7.1 102.7 (0.67, 0.32) Ex. (249) Com.(7-35) 5.0 4.8 300.0 6.2 114.8 (0.65, 0.32) Ex. (250) Com. (7-36) 5.14.1 300.0 7.3 120.6 (0.65, 0.33) Ex. (251) Com. (7-37) 5.1 4.6 300.0 6.5100.0 (0.66, 0.32) Ex. (252) Com. (7-38) 5.2 4.7 300.0 6.4 132.4 (0.67,0.33) Ex. (253) Com. (7-39) 5.0 4.1 300.0 7.4 119.4 (0.66, 0.33) Ex.(254) Com. (7-40) 4.9 4.3 300.0 6.9 124.4 (0.66, 0.32) Ex. (255) Com.(7-41) 5.3 4.5 300.0 6.7 108.5 (0.66, 0.33) Ex. (256) Com. (7-42) 5.24.2 300.0 7.2 100.9 (0.66, 0.32) Ex. (257) Com. (7-43) 5.2 4.3 300.0 7.0117.7 (0.65, 0.32) Ex. (258) Com. (7-44) 4.9 4.6 300.0 6.6 110.5 (0.66,0.33) Ex. (259) Com. (7-45) 5.2 4.3 300.0 7.0 116.3 (0.66, 0.32) Ex.(260) Com. (7-46) 4.8 4.0 300.0 7.4 120.5 (0.66, 0.33) Ex. (261) Com.(7-47) 4.9 4.7 300.0 6.4 132.9 (0.66, 0.32) Ex. (262) Com. (7-48) 5.04.1 300.0 7.3 135.4 (0.65, 0.32)

It can be seen from the results given in Table 5 above that Examplesusing the inventive compounds as the phosphorescent red host showedlower driving voltage, higher efficiency, and longer life span thanComparative Examples 6 to 10. Especially, it can be noted from Table 5above that Comparative Compounds 4 and 5 showed longer life span thanComparative Compounds 2 and 3 when being used as the phosphorescentgreen host, but showed lower efficiency and shorter life span thanComparative Compounds 2 and 3 when being used as the phosphorescent redhost.

Test Example 3 (Hole Transport Layer)

First, an ITO layer (anode) was formed on a glass substrate, and 2-TNATAwas vacuum-deposited on the ITO layer to form a hole injection layerwith a thickness of 60 nm. Subsequently, the inventive compound(5-1-5-7, 5-11-5-14, 5-17-5-31, 5-33-5-35) was vacuum-deposited with athickness of 20 nm on the hole injection layer to form a hole transportlayer. Thereafter, a light emitting layer with a thickness of 30 nm wasdeposited on the hole transport layer by doping the hole transport layerwith CBP[4,4′-N,N′-dicarbazole-bisphenyl] as a host material andIr(ppy)₃ as a dopant material in a weight ratio of 90:10. Next, BAlq wasvacuum-deposited with a thickness of 10 nm on the light emitting layerto form a hole blocking layer, and then a film of Alq₃ was formed with athickness of 40 nm to form an electron injection layer. Subsequently,LiF as halogenated alkali metal was deposited with a thickness of 0.2 nmon the electron injection layer, and then Al was deposited with athickness of 150 nm thereon to form an Al/LiF cathode. In this way, anOLED was completed.

Comparative Example 11

An OLED was manufactured in the same manner as described in Test Example3, except that Comparative Compound 6(N4,N4′-di(naphthalene-1-yl)-N4,N4′-diphenyl-[1,1′-biphenyl]-4,4′-diamine)was used as the hole transport layer material, instead of the inventivecompound.

Comparative Example 12

An OLED was manufactured in the same manner as described in Test Example3, except that the hole transport layer was formed using ComparativeCompound 7(N,N,12-triphenyl-12H-benzo[4,5]thieno[3,2-a]carbazol-9-amine), insteadof the inventive compound.

Comparative Example 13

An OLED was manufactured in the same manner as described in Test Example3, except that the hole transport layer was formed using ComparativeCompound 8(N-(9,9-dimethyl-9H-fluoren-2-yl)-N,12-diphenyl-12H-benzo[4,5]thieno[3,2-a]carbazol-9-amine),instead of the inventive compound.

Comparative Example 14

An OLED was manufactured in the same manner as described in Test Example3, except that the hole transport layer was formed using ComparativeCompound 9(N,N-di([1,1′-biphenyl]-4-yl)-12-phenyl-12H-benzo[4,5]thieno[2,3-a]carbazol-8-amine), instead of the inventive compound.

A forward bias DC voltage was applied to each of the OLEDs manufacturedin Test Example 3 and Comparative Examples 11 to 14, and ELcharacteristics of the OLED were measured by PR-650 (Photo research).Also, T95 life span was measured by life span measuring equipment (Mcscience) at a reference brightness of 300 cd/m². Table 6 below shows themeasurement results. In Table 5, Examples 262 to 290 represent theinventive OLEDs manufactured according to Test Example 3.

TABLE 6 Compound Driving Voltage Current Density (mA/cm2) Brightness(cd/m2) Efficiency (cd/A) T(95) Comp. Ex. (11) Comp. Com. (6) 6.2 7.5300.0 4.0 74.0 Comp. Ex. (12) Comp. Com. (7) 5.5 5.3 300.0 5.7 94.9Comp. Ex. (13) Comp. Com. (8) 5.1 5.8 300.0 4.8 93.1 Comp. Ex. (14)Comp. Com. (9) 5.4 5.2 300.0 5.8 60.5 Ex. (262) Com. (5-1) 5.1 4.8 300.06.2 124.5 Ex. (263) Com. (5-2) 5.1 4.8 300.0 6.2 106.7 Ex. (264) Com.(5-3) 4.8 4.4 300.0 6.8 120.0 Ex. (265) Com. (5-4) 5.0 4.4 300.0 6.8127.0 Ex. (266) Com. (5-5) 5.1 4.8 300.0 6.3 105.6 Ex. (267) Com. (5-6)5.0 4.7 300.0 6.3 120.0 Ex. (268) Com. (5-10) 4.8 4.6 300.0 6.5 108.1Ex. (269) Com. (5-11) 5.1 4.5 300.0 6.7 121.3 Ex. (270) Com. (5-12) 5.04.7 300.0 6.4 107.4 Ex. (271) Com. (5-13) 4.9 4.5 300.0 6.6 97.7 Ex.(272) Com. (5-14) 4.8 4.8 300.0 6.3 115.3 Ex. (273) Com. (5-17) 4.9 4.6300.0 6.5 121.9 Ex. (274) Com. (5-18) 4.8 4.9 300.0 6.2 108.2 Ex. (275)Com. (5-19) 4.9 4.6 300.0 6.5 119.7 Ex. (276) Com. (5-20) 5.0 4.8 300.06.2 113.9 Ex. (277) Com. (5-21) 4.8 4.9 300.0 6.2 112.5 Ex. (278) Com.(5-22) 5.1 4.4 300.0 6.8 110.2 Ex. (279) Com. (5-23) 4.8 4.5 300.0 6.7127.2 Ex. (280) Com. (5-24) 4.6 4.2 300.0 7.1 112.9 Ex. (281) Com.(5-25) 4.7 4.6 300.0 6.5 108.3 Ex. (282) Com. (5-26) 4.9 4.1 300.0 7.3102.1 Ex. (283) Com. (5-27) 4.8 4.1 300.0 7.3 141.7 Ex. (284) Com.(5-28) 4.7 4.5 300.0 6.7 128.9 Ex. (285) Com. (5-29) 4.8 4.4 300.0 6.8122.6 Ex. (286) Com. (5-30) 4.5 4.3 300.0 6.9 122.0 Ex. (287) Com.(5-31) 4.5 4.5 300.0 6.6 114.4 Ex. (288) Com. (5-33) 4.8 4.1 300.0 7.3126.6 Ex. (289) Com. (5-34) 4.8 4.1 300.0 7.3 105.9 Ex. (290) Com.(5-35) 4.5 4.2 300.0 7.2 148.4

It can be seen from the results given in Table 6 above that Examplesusing the inventive compounds as the hole transport layer showed lowerdriving voltage, higher efficiency, and longer life span thanComparative Examples 11 to 14. This is believed because compoundssubstituted by an aryl group at one of positions R₁ to R₄ and R₁₁ to R₁₄of the core and containing an aryl amine group at another position moreeasily transport holes into the light emitting layer due to a decreasedHOMO level, and thus show low driving voltage, resulting in long lifespan.

Test Example 4 (Emission-Auxiliary Layer)

First, an ITO layer (anode) was formed on a glass substrate, and 2-TNATAwas vacuum-deposited on the ITO layer to form a hole injection layerwith a thickness of 60 nm. Subsequently, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (Comparative Compound 6) was vacuum-deposited with athickness of 20 nm on the hole injection layer to form a hole transportlayer. Next, the inventive compound (5-1-5-7, 5-11-5-14, 5-17-5-31,5-33-5-35, 5-47-5-51) was vacuum-deposited with a thickness of 20 nm onthe hole transport layer to form an emission-auxiliary layer.Thereafter, a light emitting layer with a thickness of 30 nm wasdeposited on the emission-auxiliary layer by doping theemission-auxiliary layer with CBP[4,4′-N,N′-dicarbazole-bisphenyl] as ahost material and Ir(ppy)₃ as a dopant material in a weight ratio of95:5. Also, BAlq was vacuum-deposited with a thickness of 10 nm on thelight emitting layer to form a hole blocking layer, and then a film ofAlq₃ was formed with a thickness of 40 nm to form an electron injectionlayer. Subsequently, LiF as halogenated alkali metal was deposited witha thickness of 0.2 nm on the electron injection layer, and then Al wasdeposited with a thickness of 150 nm thereon to form an Al/LiF cathode.In this way, an OLED was completed.

Comparative Example 15

An OLED was manufactured in the same manner as described in Test Example4, except that Comparative Compound6(N4,N4′-di(naphthalene-1-yl)-N4,N4′-diphenyl-[1,1′-biphenyl]-4,4′-diamine)was used as the emission-auxiliary layer material, instead of theinventive compound.

Comparative Example 16

An OLED was manufactured in the same manner as described in Test Example4, except that the emission-auxiliary layer was formed using ComparativeCompound 7(N,N,12-triphenyl-12H-benzo[4,5]thieno[3,2-a]carbazol-9-amine), insteadof the inventive compound.

Comparative Example 17

An OLED was manufactured in the same manner as described in Test Example4, except that the emission-auxiliary layer was formed using ComparativeCompound 8(N-(9,9-dimethyl-9H-fluoren-2-yl)-N,12-diphenyl-12H-benzo[4,5]thieno[3,2-a]carbazol-9-amine),instead of the inventive compound.

Comparative Example 18

An OLED was manufactured in the same manner as described in Test Example4, except that the emission-auxiliary layer was formed using ComparativeCompound 9(N,N-di([1,1′-biphenyl]-4-yl)-12-phenyl-12H-benzo[4,5]thieno[2,3-a]carbazol-8-amine),instead of the inventive compound.

A forward bias DC voltage was applied to each of the OLEDs manufacturedin Test Example 4 and Comparative Examples 15 to 18, and ELcharacteristics of the OLED were measured by PR-650 (Photo research).Also, T95 life span was measured by life span measuring equipment (Mcscience) at a reference brightness of 300 cd/m². Table 7 below shows themeasurement results. In Table 7, Examples 291 to 324 represent theinventive OLEDs manufactured according to Test Example 4.

TABLE 7 Compound Driving Voltage Current Density (mA/cm2) Brightness(cd/m2) Efficiency (cd/A) T(95) Comp. Ex. (15) Comp. Com. (6) 5.9 6.3300.0 4.8 86.3 Comp. Ex. (16) Comp. Com. (7) 5.1 5.8 300.0 5.2 91.3Comp. Ex. (17) Comp. Com. (8) 5.7 5.8 300.0 5.2 92.7 Comp. Ex. (18)Comp. Com. (9) 5.7 5.8 300.0 5.2 89.1 Ex. (291) Com. (5-1) 5.0 4.0 300.07.4 109.4 Ex. (292) Com. (5-2) 5.2 3.8 300.0 7.8 112.5 Ex. (293) Com.(5-3) 5.2 3.9 300.0 7.6 97.9 Ex. (294) Com. (5-4) 5.2 3.9 300.0 7.6104.9 Ex. (295) Com. (5-5) 5.0 4.1 300.0 7.4 129.8 Ex. (296) Com. (5-6)4.9 3.7 300.0 8.0 111.8 Ex. (297) Com. (5-7) 5.2 4.0 300.0 7.4 101.1 Ex.(298) Com. (5-11) 5.0 3.9 300.0 7.7 97.9 Ex. (299) Com. (5-12) 5.2 3.8300.0 8.0 121.1 Ex. (300) Com. (5-13) 5.1 4.0 300.0 7.5 126.1 Ex. (301)Com. (5-14) 5.0 4.0 300.0 7.6 118.2 Ex. (302) Com. (5-17) 5.1 4.1 300.07.3 97.0 Ex. (303) Com. (5-18) 5.0 4.1 300.0 7.2 104.0 Ex. (304) Com.(5-19) 5.1 3.9 300.0 7.8 103.0 Ex. (305) Com. (5-20) 4.9 3.6 300.0 8.4109.0 Ex. (306) Com. (5-21) 5.1 3.7 300.0 8.1 107.8 Ex. (307) Com.(5-22) 5.1 3.5 300.0 8.5 113.2 Ex. (308) Com. (5-23) 5.2 3.7 300.0 8.1116.2 Ex. (309) Com. (5-24) 5.0 3.9 300.0 7.8 142.7 Ex. (310) Com.(5-25) 5.1 3.6 300.0 8.3 100.0 Ex. (311) Com. (5-26) 5.1 3.9 300.0 7.7120.4 Ex. (312) Com. (5-27) 5.1 4.0 300.0 7.4 134.9 Ex. (313) Com.(5-28) 5.0 3.7 300.0 8.2 146.0 Ex. (314) Com. (5-29) 5.2 4.0 300.0 7.5142.3 Ex. (315) Com. (5-30) 5.0 3.9 300.0 7.7 114.9 Ex. (316) Com.(5-31) 5.0 3.7 300.0 8.2 123.9 Ex. (317) Com. (5-33) 5.0 4.0 300.0 7.4136.8 Ex. (318) Com. (5-34) 4.8 3.7 300.0 8.1 130.5 Ex. (319) Com.(5-35) 4.9 4.0 300.0 7.6 130.9 Ex. (320) Com. (5-47) 4.6 3.3 300.0 9.0125.3 Ex. (321) Com. (5-48) 4.5 3.7 300.0 8.1 136.8 Ex. (322) Com.(5-49) 4.4 3.5 300.0 8.7 123.2 Ex. (323) Com. (5-50) 4.7 3.4 300.0 8.9140.8 Ex. (324) Com. (5-51) 4.5 4.0 300.0 7.5 129.5

It can be seen from the results given in Table 6 that when the inventivecompounds were used as the emission-auxiliary layer between the holetransport layer and the light emitting layer in order to increaseefficiency and life span, luminous efficiency and life span wereimproved as compared to when the comparative compounds were used as theemission-auxiliary layer. This is believed because use of theemission-auxiliary layer with a HMO level that lies between the HOMOlevel of Comparative Compound 6 used as the hole transport layer and theHOMO level of the light emitting layer leads to high efficiency and longlife span.

Test Example 5 (Phosphorescent Red Host)

First, an ITO layer (anode) was formed on a glass substrate, and 2-TNATAwas vacuum-deposited on the ITO layer to form a hole injection layerwith a thickness of 60 nm. Subsequently, NPD was vacuum-deposited with athickness of 60 nm on the hole injection layer to form a hole transportlayer. Next, a light emitting layer with a thickness of 30 nm wasdeposited on the hole transport layer by doping the hole transport layerwith the inventive compound (8-2, 8-3, 8-7, 8-8, 8-10, 8-22, 8-23, 8-27,8-28, 8-35, 9-2, 9-3, 9-6, 9-8, 9-12, 9-14, 9-17, 9-22, 9-23, 9-29,9-32, 9-36) as a host material and (piq)2Ir(acac)[bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] as a dopantmaterial in a weight ratio of 95:5. Also, BAlq was vacuum-deposited witha thickness of 10 nm on the light emitting layer to form a hole blockinglayer, and a film of Alq3 was formed with a thickness of 40 nm on thehole blocking layer to form an electron injection layer. Next, LiF ashalogenated alkali metal was deposited with a thickness of 0.2 nm on theelectron injection layer, and then Al was deposited with a thickness of150 nm thereon to form an Al/LiF cathode. In this way, an OLED wascompleted.

Comparative Example 19

An OLED was manufactured in the same manner as described in Test Example5, except that Comparative Compound[12-(4,6-diphenyl-1,3,5-triazin-2-yl)-12H-benzo[4,5]thieno[2,3-a]carbazole]was used as the host material of the light emitting layer, instead ofthe inventive compound.

Comparative Example 20

An OLED was manufactured in the same manner as described in Test Example5, except that Comparative Compound 11[12-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)-12H-benzo[4,5]thieno[2,3-a]carbazole] was used as the host material of the lightemitting layer, instead of the inventive compound.

Comparative Example 21

An OLED was manufactured in the same manner as described in Test Example5, except that Comparative Compound12[12-(4,6-diphenyl-1,3,5-triazin-2-yl)-12H-benzo[4,5]thieno[3,2-a]carbazole]was used as the host material of the light emitting layer, instead ofthe inventive compound.

Comparative Example 22

An OLED was manufactured in the same manner as described in Test Example5, except that Comparative Compound13[12-(4-([1,1′-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-12H-benzo[4,5]thieno[3,2-a]carbazole]was used as the host material of the light emitting layer, instead ofthe inventive compound.

Comparative Example 23

An OLED was manufactured in the same manner as described in Test Example5, except that Comparative Compound14[14-(4,6-diphenylpyrimidin-2-yl)-14H-benzo[c]benzo[4,5]thieno[2,3-a]carbazole]was used as the host material of the light emitting layer, instead ofthe inventive compound.

Comparative Example 24

An OLED was manufactured in the same manner as described in Test Example5, except that Comparative Compound15[14-(4,6-diphenylpyrimidin-2-yl)-14H-benzo[c]benzo[4,5]thieno[3,2-a]carbazole]was used as the host material of the light emitting layer, instead ofthe inventive compound.

Comparative Example 25

An OLED was manufactured in the same manner as described in Test Example5, except that Comparative Compound14[14-(4,6-diphenyl-1,3,5-triazin-2-yl)-14H-benzo[c]benzo[4,5]thieno[2,3-a]carbazole]was used as the host material of the light emitting layer, instead ofthe inventive compound.

Comparative Example 26

An OLED was manufactured in the same manner as described in Test Example5, except that Comparative Compound15[14-(4,6-diphenyl-1,3,5-triazin-2-yl)-14H-benzo[c]benzo[4,5]thieno[3,2-a]carbazole]was used as the host material of the light emitting layer, instead ofthe inventive compound.

A forward bias DC voltage was applied to each of the OLEDs manufacturedin Test Example 5 and Comparative Examples 19 to 26, and ELcharacteristics of the OLED were measured by PR-650 (Photo research).Also, T95 life span was measured by life span measuring equipment (Mcscience) at a reference brightness of 2500 cd/m2. Table 10 below showsthe measurement results. In Table 10, Examples 325 to 346 represent theinventive OLEDs manufactured according to Test Example 5.

TABLE 8 current Driving Density Brightness Efficiency CIE CompoundVoltage (mA/cm²) (cd/m²) (cd/A) T(95) x y Comp. Ex. (19) Comp. Com.(10)5.6 22.7 2500 11.0 83.4 0.67 0.34 Comp. Ex. (20) Comp. Com (11) 5.4 20.32500 12.3 87.1 0.66 0.34 Comp. Ex. (21) Comp. Com (12) 5.6 20.0 250012.5 80.9 0.66 0.35 Comp. Ex. (22) Comp. Com (13) 5.3 19.4 2500 12.982.3 0.65 0.34 Comp. Ex. (23) Comp. Com (14) 5.3 15.6 2500 16.0 125.90.66 0.33 Comp. Ex. (24) Comp. Com (15) 5.4 14.7 2500 17.0 124.8 0.660.35 Comp. Ex. (25) Comp. Com (16) 5.4 15.3 2500 16.3 122.6 0.67 0.35Comp. Ex. (26) Comp. Com (17) 5.5 15.0 2500 16.7 126.1 0.66 0.35 Ex.(325) Com.(8-2) 5.1 14.6 2500 17.2 142.5 0.67 0.35 Ex. (326) Com.(8-3)5.1 13.9 2500 18.0 134.0 0.65 0.35 Ex. (327) Com.(8-7) 5.0 14.5 250017.3 136.7 0.65 0.35 Ex. (328) Com.(8-8) 5.0 13.9 2500 18.0 135.3 0.650.33 Ex. (329) Com.(8-10) 5.0 14.2 2500 17.6 132.0 0.67 0.34 Ex. (330)Com.(8-22) 5.0 14.1 2500 17.8 128.0 0.66 0.34 Ex. (331) Com.(8-23) 5.115.4 2500 16.2 132.0 0.66 0.33 Ex. (332) Com.(8-27) 5.0 14.4 2500 17.4129.4 0.67 0.35 Ex. (333) Com.(8-28) 5.1 14.9 2500 16.8 134.4 0.65 0.34Ex. (334) Com.(8-35) 5.0 15.3 2500 16.4 131.1 0.66 0.35 Ex. (335)Com.(9-2) 4.9 14.3 2500 17.5 134.4 0.65 0.35 Ex. (336) Com.(9-3) 4.814.2 2500 17.6 136.8 0.65 0.34 Ex. (337) Com.(9-6) 5.0 15.5 2500 16.2138.5 0.66 0.34 Ex. (338) Com.(9-8) 4.9 14.2 2500 17.6 131.0 0.66 0.35Ex. (339) Com.(9-12) 4.8 14.4 2500 17.3 133.1 0.65 0.35 Ex. (340)Com.(9-14) 4.8 15.4 2500 16.2 130.7 0.65 0.34 Ex. (341) Com.(9-17) 4.714.5 2500 17.3 128.2 0.66 0.34 Ex. (342) Com.(9-22) 4.9 15.3 2500 16.3131.4 0.66 0.33 Ex. (343) Com.(9-23) 4.8 15.4 2500 16.2 135.9 0.67 0.34Ex. (344) Com.(9-29) 4.8 14.9 2500 16.8 134.8 0.66 0.33 Ex. (345)Com.(9-32) 4.9 15.5 2500 16.1 130.7 0.67 0.35 Ex. (346) Com.(9-36) 5.015.1 2500 16.6 136.4 0.65 0.33

It can be seen from the results in Table 8, above, that the inventivecompounds showed lower driving voltage and higher efficiency, comparedto the compounds of Comparative Examples 19 to 22.

Particularly it was shown that the compounds of Comparative Example 19(Comp. Com (10)) and Comparative Example 21 (Comp. Com (12)) having twosame substituents (phenyl groups) as Ar5 and Ar6 on the triazinederivative showed lower driving voltage and increased lifespan, comparedto the compounds of Comparative Example 20 (Comp. Com (11)) andComparative Example 22 (Comp. Com 13) having two different substituentsas Ar₅ and Ar₆ on the triazine derivataive, all of them having the samecore structure and triazine derivative on the core.

Based on the result, the inventive compounds each having differentsubstituents (Ar₅, Ar₆) (unsymmetrical) on the pyrimidine or triazinederivative were tested, compared to Comparative Examples 23 to 26, andfound that they commonly have lower driving voltage and increasedlifespan. This result tells that in the inventive compounds havingdifferent substituents (unsymmetrical) on the pyrimidine or triazinederivative, driving voltage is lower and lifespan is longer, whileefficiency is not different from, than the compounds having samesubstituents (symmetrical)

Generally, hole moves faster than electron by 1,000 times in an OLEDmaterial and thereby hole stay may happen in the light emitting layerand as a result driving voltage may increase and lifespan may decreasecausing reduction in charge balance. Accordingly, believing that theinventive compounds may increase charge balance by increasing electronsin the light emitting layer from the lower driving voltage and increasedlifespan while maintaining efficiency, Comparative Compound 14 (Ar₅=Ar₆)and Compound 9-2 (Ar₅≠Ar₆) were tested for HOD (FIG. 3) and EOD (FIG. 2)and it was found that Comparative Compound 14 shows a relativelysuperior hole mobility to Compound 9-2 and Compound 9-2 shows arelatively superior electron mobility to Comparative Compound 14.

In conclusion, it is believed that the inventive compounds having twodifferent substituents (Ar₅, Ar₆) on the pyrimidine or triazinederivative when they are used as a host material in the light emittinglayer, can bind with the holes stayed in the layer from their fastelectron mobility and thereby they can increase charge balance, loweringdriving voltage and increasing lifespan.

It is obvious that even when the inventive compounds are used in otherorganic material layers of an OLED, for example, an electron injectionlayer, an electron transport layer, and a hole injection layer, the sameeffects can be obtained.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

What is claimed is:
 1. A compound represented by Formula 1 below,

wherein R₁ to R₄ and R₁₁ to R₁₄ are each independently selected from thegroup consisting of hydrogen, deuterium, halogen, a C₆-C₆₀ aryl group, afluorenyl group, a fused ring group of a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring, a C₂-C₆₀ heterocyclic group containing at leastone heteroatom selected from the group consisting of O, N, S, Si, and P,-L-N(R′)(R″), a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₁-C₃₀alkoxy group, and a C₆-C₃₀ aryloxy group; R₂₁ and R₂₂ together form amonocyclic or fused or non-fused polycyclic ring selected from the groupconsisting of a C₃-C₆₀ aliphatic ring, a C₆-C₆₀ aromatic ring, and aC₂-C₆₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P; X and Y are eachindependently S, O, or SiR₃₁R₃₂, wherein R₃₁ and R₃₂ are eachindependently hydrogen, a C₆-C₆₀ aryl group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P, or a C₁-C₅₀ alkyl group, R₃₁ and R₃₂ beingoptionally substituted by one or more substituents selected from thegroup consisting of deuterium, halogen, a silane group, a cyano group, anitro group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀alkenyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted bydeuterium, a C₂-C₂₀ eterocyclic group, a C₃-C₂₀ cycloalkyl group, aC₇-C₂₀ arylalkyl group, and a C₈-C₂₀ arylalkenyl group, m and n are each0 or 1 with the proviso that m+n is an integer equal to or greater than1 ; L is selected from the group consisting of a single bond; a C₆-C₆₀arylene group; a fluorenylene group; a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom selected from the group consisting ofO, N, S, Si, and P; and a bivalent aliphatic hydrocarbon group, wherein,the arylene group, the fluorenyl group, the heterocyclic group, and thebivalent aliphatic hydrocarbon group are optionally substituted by oneor more substituents selected from the group consisting of a nitrogroup, a cyano group, a halogen group, a C₁-C₂₀ alkyl group, a C₆-C₂₀aryl group, a C₂-C₂₀ heterocyclic group, a C₁-C₂₀ alkoxy group, and anamino group); Ar is a compound represented by Formula 1a below,

wherein X₅ to X₇ are each independently nitrogen or C(R₅₁) with theproviso that at least one of X₅ to X₇ is N, wherein R₅₁ is selected fromthe group consisting of a C₂-C₂₀ alkyl group, a C₆-C₂₀ aryl group, aC₂-C₂₀ alkenyl group, and C₂-C₆₀ heterocyclic group containing at leastone heteroatom selected from the group consisting of O, N, S, Si, and P;Ar₅ and Ar₆ are different from each other and each selected from thegroup consisting of a substituted or unsubstituted C₆-C₆₀ aryl group, asubstituted or unsubstituted fluorenyl group, and a substituted orunsubstituted C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P,wherein Ar₅ and Ar₆ are optionally substituted by one or moresubstituents selected from the group consisting of a nitro group, acyano group, a halogen group, a C₁-C₂₀ alkyl group, a C₆-C₂₀ aryl group,a C₂-C₂₀ heterocyclic group, a C₁-C₂₀ alkoxy group, and an amino group,R′ and R″ are each independently a C₂-C₆₀ heterocyclic group containingat least one heteroatom selected from O, N, S, Si, and P, a C₆-C₂₀ arylgroup, or a fluorenyl group, R₁ to R₄, R₁₁ to R₁₄, R₅₁, R′, R″, and thering formed by R₂₁ and R₂₂ are optionally substituted by one or moresubstituents selected from the group consisting of deuterium, halogen, asilane group, a boron group, a germanium group, a cyano group, a nitrogroup, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkylgroup, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ arylgroup, a C₆-C₂₀ aryl group substituted by deuterium, a C₂-C₂₀heterocyclic group, a C₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkyl group,and a C₈-C₂₀ arylalkenyl group.
 2. The compound of claim 1, representedby one of Formulas below:

wherein R₁ to R₄, R₁₁ to R₁₄, R₂₁, R₂₂, X, L, Ar, Ar₅, Ar₆, and X₅ to X₇are the same as defined in claim
 1. 3. The compound of claim 1,represented by one of Formulas below:

wherein R₁ to R₄, R₁₁ to R₁₄, R₂₁, R₂₂, Y, L, Ar, Ar₅, Ar₆, and X₅ to X₇are the same as defined in claim
 1. 4. The compound of claim 1, whereinAr₅ is a naphthyl group.
 5. The compound of claim 1, selected from thegroup consisting of the following compounds:


6. An organic electric element comprising a first electrode, a secondelectrode, and an organic material layer disposed between the firstelectrode and the second electrode, wherein the organic material layercomprises the compound of claim
 1. 7. The organic electric element ofclaim 6, wherein the compound is a phosphorescent red host material ofthe organic material layer.
 8. The organic electric element of claim 6,wherein the organic material layer is formed with the compound by asoluble process.
 9. The organic electric element of claim 6, wherein theorganic material layer comprises at least one of a light emitting layer,a hole injection layer, a hole transport layer, an emission-auxiliarylayer, an electron injection layer, and an electron transport layer. 10.The organic electric element of claim 9, wherein the organic materiallayer comprises at least one of the light emitting layer, the holeinjection layer, and the emission-auxiliary layer, and said at least oneof the light emitting layer, the hole injection layer, and theemission-auxiliary layer comprises the compound.
 11. An electronicdevice comprising a display device, which comprises the organic electricelement of claim 6 and a control unit for driving the display device.12. The electronic device of claim 10, wherein the organic electricelement comprises at least one of an organic light emitting diode(OLED), an organic solar cell, an organic photo conductor (OPC), anorganic transistor (organic TFT), and an element for monochromatic orwhite illumination.
 13. The compound of claim 1, wherein R₁ to R₄ andR₁₁ to R₁₄ all are hydrogen.
 14. An organic electric element,comprising: a substrate; a first electrode formed on the substrate; asecond electrode; and an organic material layer formed between the firstelectrode and the second electrode, comprising a light emitting layerand the compound of claim
 1. 15. The organic electric element of claim14, wherein the organic material layer further comprises at least one ofa hole injection layer between the first electrode and the lightemitting layer and an emission-auxiliary layer between the firstelectrode and the light emitting layer or between the hole injectionlayer and the light emitting layer when the hole injection layer ispresent, and at least one of the light emitting layer, the holeinjection layer and the emission-auxiliary layer comprises the compound.16. The organic electric element of claim 14, wherein the organicmaterial layer further comprising a hole injection layer between thefirst electrode and the light emitting layer, one or more hole transportlayer between the hole injection layer and the light emitting layer, anelectron injection layer between the second electrode and the lightemitting layer, and one or more electron transport layer between theelectron injection layer and the light emitting layer.
 17. The organicelectric element of claim 16, wherein at least one of the light emittinglayer, the hole injection layer, the hole transport layer(s), theelectron injection layer and the electron transport comprises thecompound.
 18. The organic electric element of claim 14, wherein theorganic material layer further comprising a hole injection layer formedon the first electrode, a hole transport layer formed between the holeinjection layer and the light emitting layer, a hole blocking layerformed on the light emitting layer, and an electron injection layerformed between the hole blocking layer and the second electrode.
 19. Theorganic electric element of claim 14, wherein the light emitting layercomprises a host material of the compound and a dopant material.
 20. Theorganic electric element of claim 19, wherein the compound is aphosphorescent red host material of the light emitting layer.